Diastereoselective Conjugate Addition to (+)-Camphorsulfonic Acid Derived Nitroalkenes: Synthesis of α-Hydroxy and α-Amino Acids

…, PWN Christian, D Pilipauskas, AJP White…

Index: Barrett, Anthony G. M.; Braddock, D. Christopher; Christian, Paul W. N.; Pilipauskas, Daniel; White, Andrew J. P.; Williams, David J. Journal of Organic Chemistry, 1998 , vol. 63, # 17 p. 5818 - 5823

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Citation Number: 18

Abstract

Diastereoselective tandem conjugate addition of both oxygen-and nitrogen-centered nucleophiles to the novel (1 S)-10-camphorsulfonic acid derived nitroalkenes 9, 10, and 11 and ozonolysis gave the α-hydroxy and α-amino thiol acid derivatives 12, 13, and 14. In all cases, the (R)-diastereomer was formed as the major component albeit with only modest levels of selectivity (33-71% de). The structures of the products and the stereochemistry of ...