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

Jia Fu Pan, Uppala Venkatesham, Kwunmin Chen

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)9345-9347
Number of pages3
JournalTetrahedron Letters
Volume45
Issue number51
DOIs
Publication statusPublished - 2004 Dec 13

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Lewis Acids
X ray analysis
Alkenes
Hydroxyl Radical
X-Rays
Single crystals
glyoxylic acid

Keywords

  • Diastereoselective
  • Glyoxylate-ene reaction
  • Stereogenic center

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile. / Pan, Jia Fu; Venkatesham, Uppala; Chen, Kwunmin.

In: Tetrahedron Letters, Vol. 45, No. 51, 13.12.2004, p. 9345-9347.

Research output: Contribution to journalArticle

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