USO09598458B2 (12) United States Patent (10) Patent No.: US 9,598.458 B2 Shimizu et al. (45) Date of Patent: Mar. 21, 2017 (54) ASYMMETRICAUXILLARY GROUP 3,687,808 A 8/1972 Merigan et al. 3,745,162 A 7/1973 Helsley 4,022,791 A 5/1977 Welch, Jr. (71) Applicant: NYTE SCIENCES JAPAN, 4,113,869 A 9, 1978 Gardner ... Kagoshima-shi (JP) 4.415,732 A 1 1/1983 Caruthers et al. 4,458,066 A 7/1984 Caruthers et al. (72) Inventors: Mamoru Shimizu, Uruma (JP); 4,500,707 A 2f1985 Caruthers et al. Takeshi Wada, Kashiwa (JP) 4,542,142 A 9, 1985 Martel et al. 4,659,774 A 4, 1987 Webb et al. 4,663,328 A 5, 1987 Lafon (73) Assignee: YESCIENCES JAPAN, 4,668,777. A 5/1987 Caruthers et al. ... Kagoshima-shi (JP) 4,725,677 A 2/1988 Koster et al. 4,735,949 A 4, 1988 Domagala et al. (*) Notice: Subject to any disclaimer, the term of this 4,840,956 A 6/1989 Domagala et al. patent is extended or adjusted under 35 3:38 A . 3. EthOester Phet al. et al. 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Comm., 1974.* C7H 23/00 (2006.01) (Continued) C07F 7/08 (2006.01) C07D 207/08 (2006.01) C07B 53/00 (2006.01) Primary Examiner — Layla Berry C07H 19/11 (2006.01) (74) Attorney, Agent, or Firm — Choate, Hall & Stewart, C07H 19/213 (2006.01) LLP. Brenda Herschbach Jarrell: Xiaodong Li C7H 2L/04 (2006.01) CO7D 405/04 (2006.01) CO7D 473/18 (2006.01) (57) ABSTRACT CO7D 473/34 (2006.01) To provide a chiral reagent or a salt thereof. The chiral (52) U.S. Cl. reagent9. has following9. chemical formula (I). In the formula CPC ............. C07H 23/00 (2013.01); C07B 53/00 (I), G' and G' are independently a hydrogen atom, a nitro (2013.01); C07D 207/08 (2013.01); C07D group (-NO), a halogen atom, a cyano group (-CN), a 405/04 (2013.01); C07D 473/18 (2013.01); group of formula (II) or (III), or both G' and G' taken C07D 473/34 (2013.01); C07F 7/0812 together to form a group of formula (IV). (2013.01); C07H I/00 (2013.01); C07H 19/11 (2013.01); C07H 19/213 (2013.01); C07H 21/04 (2013.01) (I) (58) Field of Classification Search HO HN-G None See application file for complete search history. H G3 (56) References Cited Gl G2 U.S. PATENT DOCUMENTS 2,878.264 A 3, 1959 Lunsford 3,484.473 A 12, 1969 Buckman et al. 42 Claims, 1 Drawing Sheet US 9,598.458 B2 Page 2 (56) References Cited 6.242,589 6, 2001 Cook et al. 6,248,519 6, 2001 Engel et al. 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