Study of the Reactions between Vinylmagnesium Bromide and Imines Derived from (R)??Glyceraldehyde− The Key Step in the Stereodivergent Synthesis of …

…, C Cativiela, MD Díaz??de??Villegas…

Index: Badorrey, Ramon; Cativiela, Carlos; Diaz-de-Villegas, Maria D.; Diez, Roberto; Galvez, Jose A. European Journal of Organic Chemistry, 2003 , # 12 p. 2268 - 2275

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Citation Number: 8

Abstract

Abstract A total stereodivergent method for the synthesis of enantiopure syn-and anti-2- amino-1, 3, 4-butanetriol (ABT) derivatives from inexpensive and readily available D- mannitol has been developed. Key steps include:(a) the diastereoselective addition of vinylmagnesium bromide to conveniently protected N-benzylimines derived from (R)- glyceraldehyde, and (b) the oxidative degradation of the C− C double bond of the ...