Synthesis

Copper (I)-catalyzed enantioselective 1, 3-dipolar cycloaddition of azomethine ylides with vinyl sulfones

T Llamas, RG Arrayás, JC Carretero

Index: Llamas, Tomas; Arrayas, Ramon Gomez; Carretero, Juan Carlos Synthesis, 2007 , # 6 p. 950 - 956

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Citation Number: 36

Abstract

Abstract The combination of copper (I)-Taniaphos (5 mol%) is an efficient Lewis acid catalyst for the promotion of the asymmetric 1, 3-dipolar cycloaddition of azomethine ylides to aryl vinyl sulfones, providing 3-sulfonylpyrrolidines in good yields and with nearly complete exo- selectivity and good enantiocontrol (typically 65-85% ee). The transformation of the cycloadducts into cis-2, 5-disubstituted pyrrolidines of high enantiopurity (> 99% ee) has ...