5??(Pyrrolidine??2??yl) tetrazole: Rationale for the Increased Reactivity of the Tetrazole Analogue of Proline in Organocatalyzed Aldol Reactions

A Hartikka, PI Arvidsson

Index: Hartikka, Antti; Arvidsson, Per I. European Journal of Organic Chemistry, 2005 , # 20 p. 4287 - 4295

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Citation Number: 54

Abstract

Abstract 5-[(2S)-Pyrrolidine-2-yl]-1H-tetrazole (1), ie the tetrazolic acid analogue of proline, has been found to be significant more reactive than L-proline (2) in various organocatalyzed reactions. In the organocatalyzed direct asymmetric aldol reaction, acetone was reacted with aromatic and aliphatic aldehydes to afford the resulting β-hydroxy ketones in good yields and moderate to high enantiomeric excesses. The increased reactivity of 1, as compared ...