An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile

Jia Fu Pan; Uppala Venkatesham; Kwunmin Chen

doi:10.1016/j.tetlet.2004.10.121

An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile

Jia Fu Pan, Uppala Venkatesham, Kwunmin Chen

Department of Chemistry

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

8 Citations (Scopus)

Abstract

The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.

Original language	English
Pages (from-to)	9345-9347
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2004.10.121
Publication status	Published - 2004 Dec 13

Keywords

Diastereoselective
Glyoxylate-ene reaction
Stereogenic center

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.",

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AU - Venkatesham, Uppala

AU - Chen, Kwunmin

PY - 2004/12/13

Y1 - 2004/12/13

N2 - The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.

AB - The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.

KW - Diastereoselective

KW - Glyoxylate-ene reaction

KW - Stereogenic center

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