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期刊论文
Highly Diastereoselective Enolate Addition of O-Protected r-Hydroxyacetate to (SR)-tert-Butanesulfinylimines: Synthesis of Taxol Side Chain
J. Org. Chem. 2006, 71, 1588-1591，-0001，（）：
The taxol side chain (SR,2R,3S)-N-tert-butanesulfinyl-O-Boc-3-phenylisoserine benzyl ester 4c was synthesized through a lithium enolate addition of O-Boc-R-hydroxyacetate benzyl ester 5c to benzylidene (SR)-tert-butanesulfinamide 6a in excellent yield and diastereoselectivity. By similar approach, a series of enantiopure 3-substituted isoserine benzyl esters 4 useful for the semi-syntheses of taxol derivatives were also prepared in high to excellent yields and diastereoselectivities. The diastereoselective addition mechanism was discussed on the basis of the experimental observation.
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