Aldrichimica Acta 34, 2001
1951–2001: FIFTY YEARS OF CHEMISTS HELPING CHEMISTS AldrichimicaAldrichimica AACTACTA VOL.34, NO.1 • 2001 Preparation of Optically Active α-Amino Acids Alkoxymethylenemalonates in Organic Synthesis CHEMISTS HELPING CHEMISTS 53,182-0 N,N’-Di-(tert-butoxycarbonyl)thiourea, 97% 54,548-1 (1R,2S)-1-Phenyl-2-(1-pyrrolidinyl)-1-propanol, 98% 54,897-9 (1S,2R)-1-Phenyl-2-(1-pyrrolidinyl)-1-propanol, 98% O S O This diprotected thiourea is widely used in the synthesis of heterocycles, including a ONN O H H pentacyclic guanidine system as an These norephedrine derivatives are intermediate to ptilomycalin A,1 and, recently, HO N HO N useful chiral mediators and have in the preparation of p-N,N’-bis-Boc-guanidophenol, a key intermediate for the applications in the enantioselective preparation of a series of aryl o-aroylbenzoates as serine protease inhibitors.2 CH3 CH3 addition of acetylides to carbonyl (1) Nagasawa, K. et al. Tetrahedron 2000, 56, 187. (2) Jones, P.B.; Porter, N.A. J. Am. Chem. Soc. compounds. Examples include the 54,548-1 54,897-9 1999, 121, 2753. synthesis of the HIV-1 reverse transcriptase inhibitor DMP 2661 and the enantioselective addition of diethylzinc to aldehydes.2 54,036-6 1,1-Diethoxy-3-methyl-2-butene, 97% (1) Pierce, M.E. et al. J. Org. Chem. 1998, 63, 8536. (2) Soai, K. et al. ibid. 1991, 56, 4264. OEt This acetal has been utilized in the synthesis of the related 1-alkoxy-3-phenylselenoalkenes and 3-phenylselenoalkanals,1 OEt and in the preparation of 2,2-dimethylchromenes from 54,174-5 Tri-O-acetyl-β-D-arabinosylbromide, 95% electron-deficient phenols.2 (1) Nishiyama, Y.
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