The Effect of Lewis Acids on the Stereochemistry in the Ugi Three‐Component Reaction with  D ‐ lyxo ‐Pyrroline | Zendy

Bonger Kimberly M. | Zendy; Wennekes Tom | Zendy; Filippov Dmitri V. | Zendy; Lodder Gerrit | Zendy; van der Marel Gijsbert A. | Zendy; Overkleeft Herman S. | Zendy

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The Effect of Lewis Acids on the Stereochemistry in the Ugi Three‐Component Reaction with D ‐ lyxo ‐Pyrroline

Author(s) -

Bonger Kimberly M.,

Wennekes Tom,

Filippov Dmitri V.,

Lodder Gerrit,

van der Marel Gijsbert A.,

Overkleeft Herman S.

Publication year - 2008

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200800340

Subject(s) - chemistry , ugi reaction , isocyanide , pyrroline , lewis acids and bases , aldehyde , imine , stereochemistry , wittig reaction , organic chemistry , catalysis

A library of polyhydroxylated pyrrolidines was obtained by performing a tandem Staudinger/aza‐Wittig/Ugi three‐component reaction on a L ‐ribose‐derived 4‐azido aldehyde. In this paper we describe the effect of Lewis acids on the diastereoselectivity of the final Ugi three‐component reaction step that the intermediate ( D ‐ lyxo ‐pyrroline) cyclic imine undergoes. When the Ugi reaction was performed in methanol almost exclusively pyrrolidines with a 2,3‐ cis relationship were formed. However, a significant amount of 2,3‐ trans product was formed upon addition of Lewis acids to the Ugi reaction mixture. The scope of this effect is explored by evaluating a diverse set of Lewis acids in combination with variation of other reaction parameters and the carboxylic acid/isocyanide component. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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