Efficient synthesis of chiral α,β-epoxyesters via a cyclic sulfate intermediate

Tetrahedron Letters

Volumn 39, Issue 15, 1998, Pages 2071-2074

  He, Linli ^a   Byun, Hoe Sup ^a   Bittman, Robert ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; ESTER; SULFATE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032499034     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00190-7     Document Type: Article

References (17)

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11. (b) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.; Kwong, H.; Morikawa, K.; Wang, Z.; Xu, D.; Zhang, X. J. Org. Chem. 1992, 57, 2768-2771.
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16. 12. When epoxide formation in entry 1 was attempted at rt, the product was obtained in only 40% yield. Since we did not use dry MeOH, the low yield obtained at rt may result from ring opening and/or saponification.
17. 2 provided 304 mg (93% yield, 97% ee) of epoxyester 1 as a pure product (by TLC and NMR).