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

doi:10.1016/j.tet.2007.05.091

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

Department of Chemistry

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

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 language	English
Pages (from-to)	7816-7822
Number of pages	7
Journal	Tetrahedron
Volume	63
Issue number	33
DOIs	https://doi.org/10.1016/j.tet.2007.05.091
Publication status	Published - 2007 Aug 13

Keywords

Allylation
Chiral auxiliary
Glyoxylic oxime ether
Triallylaluminum

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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",

note = "Funding Information: We wish to thank the National Science Council of the Republic of China (NSC 95-2113-M-003-003) and the National Taiwan Normal University (ORD 94-G) for financial support for this work. The X-ray crystal data, which were collected and processed by National Taiwan Normal University, are gratefully acknowledged. ",

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AU - Kulkarni, Neelesh A.

AU - Yao, Ching Fa

AU - Chen, Kwunmin

N1 - Funding Information: We wish to thank the National Science Council of the Republic of China (NSC 95-2113-M-003-003) and the National Taiwan Normal University (ORD 94-G) for financial support for this work. The X-ray crystal data, which were collected and processed by National Taiwan Normal University, are gratefully acknowledged.

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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