Nonenzymatic enantioselective acylation of racemic secondary alcohols catalyzed by a SnX2-Chiral diamine complex

Tetrahedron Letters

Volumn 37, Issue 47, 1996, Pages 8543-8546

  Oriyama, Takeshi ^b   Hori, Yoko ^a   Imai, Keisuke ^a   Sasaki, Ryosuke ^a  

^a IBARAKI UNIVERSITY   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CYCLOHEXANOL DERIVATIVE;

ACYLATION; ARTICLE; CATALYSIS; DRUG PURIFICATION; ENANTIOMER; REACTION ANALYSIS; TECHNIQUE;

EID: 0001600322     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01987-9     Document Type: Article

References (24)

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17. 6. Very recently, Vedejs reported some successful results of enantioselective acylations of meso-and racemic alcohols: (a) Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430-431.
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19. 7. Oriyama,T.; Hori, Y.; Okada, C.; Nakayama, N.; Koga, G. unpublished results.
20. 2 are very efficient reagent systems for direct conversion of alkyl benzyl ethers and alkyl silyl ethers into the corresponding esters such as acetates and benzoates: (a) Oriyama, T.; Kimura, M.; Oda, M.; Koga, G. Synlett 1993, 437-440.
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22. 9. Some successful asymmetric synthesis using this type of diamine: (a) Kobayashi, S.; Horibe, M. J. Am. Chem. Soc. 1994, 116, 9805-9806.
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24. 10. The detailed reaction mechanism is not yet made clear; however, the stereochemical results were completely identical, that is, enantiomer A is acylated faster than enantiomer B as shown in Scheme 1. (formula presented)