On the scope of diastereoselective allylation of various chiral glyoxylic oxime ethers with allyltributylstannane in the presence of a Lewis acid and triallylaluminum

Neelesh A. Kulkarni, Ching Fa Yao, Kwunmin Chen

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The nucleophilic allylation of various chiral auxiliaries derived glyoxylic oxime ethers was studied. The use of allyltributylstannane in the presence of a Lewis acid and triallylaluminum provided the corresponding homoallylic amines in high chemical yields (up to 89%) and excellent stereoselectivities (up to >99%). The stereochemical bias of the allylation is proposed.

Original languageEnglish
Pages (from-to)7816-7822
Number of pages7
JournalTetrahedron
Volume63
Issue number33
DOIs
Publication statusPublished - 2007 Aug 13

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Allylation
Lewis Acids
Amines
Stereoselectivity
glyoxylic oxime ether

Keywords

  • Allylation
  • Chiral auxiliary
  • Glyoxylic oxime ether
  • Triallylaluminum

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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title = "On the scope of diastereoselective allylation of various chiral glyoxylic oxime ethers with allyltributylstannane in the presence of a Lewis acid and triallylaluminum",
abstract = "The nucleophilic allylation of various chiral auxiliaries derived glyoxylic oxime ethers was studied. The use of allyltributylstannane in the presence of a Lewis acid and triallylaluminum provided the corresponding homoallylic amines in high chemical yields (up to 89{\%}) and excellent stereoselectivities (up to >99{\%}). The stereochemical bias of the allylation is proposed.",
keywords = "Allylation, Chiral auxiliary, Glyoxylic oxime ether, Triallylaluminum",
author = "Kulkarni, {Neelesh A.} and Yao, {Ching Fa} and Kwunmin Chen",
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T1 - On the scope of diastereoselective allylation of various chiral glyoxylic oxime ethers with allyltributylstannane in the presence of a Lewis acid and triallylaluminum

AU - Kulkarni, Neelesh A.

AU - Yao, Ching Fa

AU - Chen, Kwunmin

PY - 2007/8/13

Y1 - 2007/8/13

N2 - The nucleophilic allylation of various chiral auxiliaries derived glyoxylic oxime ethers was studied. The use of allyltributylstannane in the presence of a Lewis acid and triallylaluminum provided the corresponding homoallylic amines in high chemical yields (up to 89%) and excellent stereoselectivities (up to >99%). The stereochemical bias of the allylation is proposed.

AB - The nucleophilic allylation of various chiral auxiliaries derived glyoxylic oxime ethers was studied. The use of allyltributylstannane in the presence of a Lewis acid and triallylaluminum provided the corresponding homoallylic amines in high chemical yields (up to 89%) and excellent stereoselectivities (up to >99%). The stereochemical bias of the allylation is proposed.

KW - Allylation

KW - Chiral auxiliary

KW - Glyoxylic oxime ether

KW - Triallylaluminum

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U2 - 10.1016/j.tet.2007.05.091

DO - 10.1016/j.tet.2007.05.091

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SP - 7816

EP - 7822

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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