Practical optical resolution of dl-muscone using tartaric acid derivatives as a chiral auxiliary

Tetrahedron Letters

Volumn 46, Issue 20, 2005, Pages 3457-3460

  Takabe, Kunihiko ^a   Sugiura, Masataka ^a   Asumi, Yuya ^a   Mase, Nobuyuki ^a   Yoda, Hidemi ^a   Shimizu, Hiroyasu ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

Author keywords

(R) ( ) Muscone; Chiral auxiliary; Optical resolution

Indexed keywords

ACETAL DERIVATIVE; FORMIC ACID DERIVATIVE; MUSCONE; N,N' DIBENZYL LEVO TARTARAMIDE; TARTARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ACETALIZATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CRYSTALLIZATION; DIASTEREOISOMER; OPTICAL RESOLUTION; SEPARATION TECHNIQUE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 17844372199     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.119     Document Type: Article

References (24)

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18. Previously, we reported that enzymatic resolution of racemic muscone derivatives such as alcohol and oxime was investigated. Chiral (R)-muscone with 99% ee was obtained via lipase AK-catalyzed acetylation of the corresponding hydroxy derivative. K. Takabe, T. Aoyama, Y. Kawanishi, T. Yamada, and H. Yoda 39th TEAC Vol. 1III-11 1995 Chemical Society of Japan Utsunomiya 177 178
19. Lately, Matsumura et al. reported enzymatic resolution of racemic muscone derivatives in a similar way to ours. See, Y. Matsumura, H. Fukawa, and Y. Terao Chem. Pharm. Bull. 46 9 1998 1484 1485
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21. N,N′-Dibenzyl-l-tartaramide 7 was the most effective chiral auxiliary, while other substituted tartaramide derivatives, such as N,N′-dipyrrolidinyl- and N,N′-di-(4-methoxyphenyl)methyl-l- tartaramide, gave an inseparable diastereomeric mixture
22. 3 (0.05 mmol) at indicated temperature. The reaction mixture was stirred for the indicated time, then cooled to room temperature. After evaporation of MeCN, the solid was filtered and washed with ether (10 mL). The filtrate was concentrated to give a crude oil, which was purified by column chromatography (silica gel, hexane/ethyl acetate as an eluent) to give a mixture of diastereomers 8 in excellent yield. These diastereomers were separated by recrystallization from MeOH to give (R)-8 as a colorless solid with >99% de determined by chiral HPLC using CHIRALPAK AD. The acetal 8 would be used for the enantiopurity determination of muscone 1, as the acetalization of 1 quantitatively proceeded
23. 4: C, 74.42; H, 8.82; N, 5.10. Found: C, 74.36; H, 9.13; N, 4.91
24. 3c