Diastereoselective allylation of α-ketoamides bearing camphor N-tosylpyrazolidinone auxiliary: Efficient synthesis of highly optically active two stereoisomers

Jung Hsuan Chen; Uppala Venkatesham; Li Chen Lee; Kwunmin Chen

doi:10.1016/j.tet.2005.10.042

Diastereoselective allylation of α-ketoamides bearing camphor N-tosylpyrazolidinone auxiliary: Efficient synthesis of highly optically active two stereoisomers

Jung Hsuan Chen, Uppala Venkatesham, Li Chen Lee, Kwunmin Chen

Department of Chemistry

Research output: Contribution to journal › Article

18 Citations (Scopus)

Abstract

Complementary allylation conditions were developed for the synthesis of both diastereomers of tertiary homoallylic alcohols. Treatment of camphor N-tosylpyrazolidinone derived α-ketoamides with allyltributylstannane afforded both the individual homoallylic alcohols in high optical purity (up to 98% de) when the reaction was carried out in the presence of Sn(OTf)₂ and PdCl₂, respectively. The stereochemical outcome and reversal of stereoselectivity in the reaction are proposed based on ¹³C NMR and FTIR studies.

Original language	English
Pages (from-to)	887-893
Number of pages	7
Journal	Tetrahedron
Volume	62
Issue number	5
DOIs	https://doi.org/10.1016/j.tet.2005.10.042
Publication status	Published - 2006 Jan 30

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Keywords

Allylation
Chiral auxiliary
Reversal of stereoselectivity

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Chen, J. H., Venkatesham, U., Lee, L. C., & Chen, K. (2006). Diastereoselective allylation of α-ketoamides bearing camphor N-tosylpyrazolidinone auxiliary: Efficient synthesis of highly optically active two stereoisomers. Tetrahedron, 62(5), 887-893. https://doi.org/10.1016/j.tet.2005.10.042

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AU - Chen, Kwunmin

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KW - Reversal of stereoselectivity

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10.1016/j.tet.2005.10.042