The effect of Lewis acids on the stereochemistry in the Ugi three-component reaction with D-lyxo-pyrroline

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

doi:10.1002/ejoc.200800340

The effect of Lewis acids on the stereochemistry in the Ugi three-component reaction with D-lyxo-pyrroline

Kimberly M. Bonger, Tom Wennekes, Dmitri V. Filippov, Gerrit Lodder, Gijsbert A. van der Marel, Herman S. Overkleeft^*

^*Corresponding author for this work

Leiden University

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

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.

Original language	English
Pages (from-to)	3678-3688
Journal	European Journal of Organic Chemistry
Volume	2008
Issue number	21
DOIs	https://doi.org/10.1002/ejoc.200800340
Publication status	Published - Jul 2008
Externally published	Yes

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title = "The effect of Lewis acids on the stereochemistry in the Ugi three-component reaction with D-lyxo-pyrroline",

abstract = "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.",

author = "Bonger, {Kimberly M.} and Tom Wennekes and Filippov, {Dmitri V.} and Gerrit Lodder and {van der Marel}, {Gijsbert A.} and Overkleeft, {Herman S.}",

year = "2008",

month = jul,

doi = "10.1002/ejoc.200800340",

language = "English",

volume = "2008",

pages = "3678--3688",

journal = "European Journal of Organic Chemistry",

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T1 - The effect of Lewis acids on the stereochemistry in the Ugi three-component reaction with D-lyxo-pyrroline

AU - Bonger, Kimberly M.

AU - Wennekes, Tom

AU - Filippov, Dmitri V.

AU - Lodder, Gerrit

AU - van der Marel, Gijsbert A.

AU - Overkleeft, Herman S.

PY - 2008/7

Y1 - 2008/7

N2 - 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.

AB - 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.

U2 - 10.1002/ejoc.200800340

DO - 10.1002/ejoc.200800340

M3 - Article

SN - 0075-4617

VL - 2008

SP - 3678

EP - 3688

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 21

ER -

The effect of Lewis acids on the stereochemistry in the Ugi three-component reaction with D-lyxo-pyrroline

Abstract

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