1061 Index Page numbers in italics indicate figures and tables a 2-acetylfuran 834 N,O-Acetal trimethylsilyl ether 217 Acetylpyrroles 834 Acetal substitution 231 Acid anhydrides 414 Acetalization 494, 892 – reaction catalyzed by In(III) 414 – by transition-metal catalysts 892 Acid catalysis 56 – i-Pr3SiOTf-mediated intramolecular – for high chemoselectivity 56 494 Acidity constant 36 – of aldehydes and ketones 444 AcOTf 445 Acetals 473–485, 574–575 Acrolein 15, 55, 764 – Hosomi–Sakurai allylation 475 – 1,3-dipolar cycloaddition 15 – protection 574–575 – Diels-Alder reaction 55 –R3SiX-promoted reactions 473–485 Acrolein derivatives 755 β-Acetamido Ketones 558 Acroleins 192 – One-Pot Multicomponent Synthesis – cycloaddition of 2-substituted 192 558 Acrylamides 194, 517 Acetates 445 – cycloaddition 517 • – conversion of THP and MOM ethers – cycloaddition promoted by BF3 OEt2 445 194 Acetic acid 414 Acrylic acids 193 – reaction catalyzed by In(III) 414 – catalyst 193 acetogenin(−)-mucocin 564 Acrylic esters 295 Acetone cyanohydrin 277 –[2+ 2]cycloaddition reaction 295 Acetonide 481 N-acryliminoacetates 590 Acetophenone 262, 264, 676, 774 – Mannich-type reactions 590 –Bu3SnH reduction 264 3-acryloyl-2-oxazolidinone 614, 667 – catalytic asymmetric cyanation 774 Acryloyloxazolidinone 765 – cyanation, La catalyzed 672 Actinidiolide 953 1,2-trans-acetoxy alcohols 842 Acyclic epoxide 682 4-acetoxy-1,3-dioxane 482 Acyclic epoxy alcohols 785 Acetylene 363, 930–935 – one-pot synthesis 785 – addition of Imines Cu catalyzed Acyclic siloxydiene 998 930–935 N-acyl quinolinium 269 – intramolecular reaction 363 – cyanide additions 269 Acetylenic alcohols 355 N-acyl-α-imino phosphonates 921 Acetylenic Schmidt reaction 1011 O-acyl-cyanohydrins 605 Acetylenic sila–Cope rearrangement 1006 1-acyl-3,5-dimethylpyrazoles 951 – Au catalyzed 1006 2-acyl aziridines 612 Acid Catalysis in Modern Organic Synthesis.EditedbyH.YamamotoandK.Ishihara Copyright 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN: 978-3-527-31724-0 1062 Index N-acyl thiazolidine-2-thiones 741 Adjacent Basic Sites 60 Acyl-1,3-oxazolidin-2-ones 614 Aflatoxin B2 6 Acyl-Claisen rearrangements 147 Ag(I) complexes 964 Acyl-Pictet–Spengler reaction 73 Ag(I) Lewis acids 987–1011 Acylal 445 Agelastatin A 443 – formation and hydrolysis 445 AgNO3 991 Acylals 575 AgNTf2 989, 991 – formation and Cleavage 575 AgOAc–PHOX complex 1000 6β-acylamido-5α-steroids 570 AgOAc–QUINAP complex 1000 Acylation 408, 409, 566–567, 574 AgOTf 990, 994 – by Bismuth salts 566 Al catalysts for ene reactions 256–260 – In(III) Lewis acids catalyzed 408 – Al catalyzed 256–260 – of alcohols and phenols 574 – substrates 256 – of electron-rich aromatic compounds Al(III) Lewis acids 241–336 409 – preparation 248, 251 Acylation reaction 245–247 Al(Oi-Pr)3 274, 276, 331 – Al(III) catalyzed 245–247 Al(salen) complex 272, 284, 291 Acylhydrazone 197 – structure 291 – reaction with cyclopentadiene 197 Al[(R,R)-salen]Cl complex 293 Acylhydrazones 11 Al[(S,S)-salen]Cl 291 – enantioselective allylation 11 Al[(S,S)-salen]N3 291 N-acylhydrazones 471, 911 Alanine methyl ester imine 975 – enantioselective free-radical additions – alkylation 975 911 AlAr3(THF) 732 N-acylhydrazones 399 ALB-cyclohexenone complex 287 – In(OTf)3 activated 399 Alcohols 40, 414, 416, 446, 499–502, Acylhydrazono ester 160 573–574, 581, 990, 1009 N-acylimidazoles 690 – acetylation with acetic anhydride acylimidazolesN-acylimidazoles 40 – epoxidation 690 – acylation 574 N-Acyliminium generation 399 – catalytic halogenation 581 N-acyliminium ion 398, 496 – chlorination catalyzed by InCl3 3-acyloxazolidin-2-ones 614 416 N-acyloxazolidinone 754, 1050 – intramolecular addition 990 N-acyloxazoline 142 – intramolecular additions Au catalyzed Acyloxy borane catalyst 211 1009 – chiral 211 – methoxymethylation 573 Acyloxyborane 211 –R3SiX-promoted reactions 499–502 Acyloxyborane catalyst 188, 189, 190, 216 – reaction catalyzed by In(III) 414 N-acylpyridinium ions 495 – silylation 446 Acylpyroles 83 Alcoholysis 571 N-acylpyrroles 690, 709 – of epoxides 571 – addition reaction 709 Aldehyde 553–554, 728, 736, 767 – epoxidation 690 – addition of triethylaluminum 728 Acylzirconocene chlorides 497 – allylation with BINOL-Ti complex Adamantane 370 736 – carbonylation 370 – allylation with Ti-complex 736 Adamantanone 546 – asymmetric allylation Ag catalyzed Addition reaction 144–147, 162–169, 1003 396–400 – cycloaddition 767 –C=N 396–400 – remote stereocontrol of allylation – Zn(II) catalyzed 162–169 553–554 1,4-Addition reaction 391–396 Aldehyde acetals 483 Adjacent amine group 61 Aldehyde tris(trimethylsilyl)silyl 487 Index 1063 Aldehydes 11, 256, 267, 268, 271, 299, 302, –InCl3 catalyzed tandem reaction 356, 381–391, 435, 442, 443, 444, 451, 453, between arylamines and γ 435 455, 458, 485, 508, 536, 552–553, 591, 603, –InCl3-catalyzed deoxygenation of 642, 649, 649, 650, 651, 722–725, 728, aromatic 442 731–733, 736, 745, 760, 878, 880, 992, 993, –Me3Al promotes [2 + 2]cycloaddition 1005 299 – 1,2-additions 381–391 – mukaiyama aldol reaction 485 – acetalization 444 – passerini-type reaction 508 – addition of allylsilane 732, 736 – protection 444 – Al catalyzed cycloaddions 302 –(R2AlCl)-induced intermolecular ene – alkynylation 1005 reaction 256 – alkynylation catalyzed by – reaction of diketone 745 lnCl3 –TMSCl 384 – reaction with diethyl – alkynylation In(OAc)3 –RuCl3catalyzed cyanophosphonate 267 390 – reagent for asymmetric alkylation – allylation Cr catalyzed 880 728 – allylation Yb(OTf)3 catalyzed 647 – reagents for the enantioselective – arylation 732 addition 725 – asymmetric addition 878 –reationGaCl3 Catalyfed 356 – asymmetric addition of alkyl groups – Sc(OTf)3-catalyzed allylation 591 724 –SnCl2 mediated allylation 536 – asymmetric alkylation, Ti-complex – strecker-type reaction of 650 mediated 722 Aldimine 80 – asymmetric alkynylation 458 – by quanidium salt catalyst 80 – asymmetric allylations 455 Aldimine–Yb(OTf) complex 641 – asymmetric diethylzinc addition 723 3 Aldimines 73, 75, 181–182, 591, 642, 651 – asymmetric vinylation 731 – competition reaction 651 – bromoallylation 552–553 – competition reaction of 642 – catalytic allyltitanation 733 – from tryptamine 73 – catalytic enantioselective allylboration – hydrocyanation 75 11 – hydrophosphonylation Al-mediated – chemoselective oxathioactalization 272 603 – competition reaction 651 – Sc(OTf)3-catalyzed allylation 591 – competition reaction 642 – Zn(II) catalyzed 181–182 – competitive allylation reaction 649 Aldol products 85 – cyanation 649, 768 Aldol reaction 118–119, 142–144, 154–160, – cyanoalkoxycarbonylation methyl 211, 213, 250–256, 377–381, 447, 506, cyanoformate 268 537–545, 589, 606–607, 636, 637, 739–747, – cyanosilylation with TMSCN 268 825–834, 994, 996, 1001, 1002 – cyclotrimerization of catalyzed by – Al catalyzed 250–256 – asymmetric N-nitroso 1001 InCl3 453 – dithioacetalization 443 – B(III) Lewis acid promoted 209 – enantioselective addition Ag catalyzed –BINAP•silver(I)-catalyzed asymmetric 992 994 – enantioselective alkylation with – by In(III) Lewis acids 377 Grignard reagents 264 – by scandium triflate 589 – enantioselective allylation 993 – catalyzed by lanthanide triflate 637 – enantioselective – chiral catalysts for catalytic hydrophosphonylation reactions 271 enantioselective 211 – HDA reaction 760 – Cu catalyzed 911–919 – hydrophosphonylation Al-mediated – diastereo- and enantioselective 996 272 – direct asymmetric,of diazoester – In(OTf)3-catalyzed reaction 451 Zr-Binol catalyzed 834 1064 Index Aldol reaction (contd.) – intermolecular hydroamination 1010 – enoxytrichlorosilanes using chiral – intramolecular alkoxymetalation 990 Lewis base catalysts 506 – nickel-catalyzed carbonyl-ene type –In(OAc)3-enhanced Ru-catalyzed reactions 256 447 3-(2-alkenoyl)-2-oxazolidinones 875 – lanthanide Lewis acid catalyzed 636 N-(α,β-alkenoyl)oxazolidinones 141 –ofchiralsyn and Alkenyl enolates 826 anti-α-methyl-β-protected-oxy – diastereospecific synthesis 826 aldehydes 213 Alkenyl trichloroacetate 994 – scandium and yttrium catalyzed Alkenylnitrone 847 606–607 Alkenylzirconocene 826 – Sn(II) and Sn(IV) Lewis acid based Alkolysis 282 537–545 – Al(OTf)3-catalyzed 282 – Ti catalyzed 739–747 Alkoxo titanium complexes 796 – 2-trimethylsilyloxyfuran with 2-Alkoxy-2-phenylethanol 1049 aldehydes 745 1-alkoxy-3-nitroalkanes 479 – with Lewis acids 142–144 2-alkoxy-1,4-pentadien-3-one 616 – with LPDE 118 β-alkoxy carbonyl compounds 473 – with trimethoxysilyl enolates 1002 Alkoxy dienones 617 – zirconium catalyzed 825–834 Alkoxyazetidines 990 – Zn(II) catalyzed 154–160 N-alkoxycarbonylamino sulfones 555 Aldol-tishchenko reaction 702–706, 706, Alkoxyepoxides 280 707, 834 Alkoxysilanes 470 – lanthanide catalyzed 702–706 Tert-alkyl chloride 242, 244 – reaction pathway 706 Tert-alkyl fluoride 242 – using a La(OTf)3/(R)-BINOL/BuLi Tert-alkyl–alkynyl coupling 242, 244 catalyst 707 2-alkyl-2-adamantanol 181 – with chiral Yb(OTf)3 complex 707 2-alkyl-2-aryl-3,4-dimethyl-5- – Zr catalyzed 834 phenyloxazolidines 617 Aldol-type additions 917, 919 4-alkyl-1,3-dioxanes 482 – of malonic acid hemithioesters to Alkyl alkynes 796 aldehydes 917 – intermolecular hydroamination 796 – of nitriles to ketones 919 Alkyl aluminum 301 Aldol-type reaction 209–214, 473–474, 495 Alkylarylsulfoxides 786 – acetals and subsequent elimination of – asymmetric synthesis 786 tetrahydrothiophene 495 Alkyl dimethylsilyl ethers 485 – boron Lewis acids promoted 209 Alkyl halides 449 – with silyl enolates 473–474 – coupling reactions 449 Aldoxime