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 › peer-review

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

Keywords

Allylation
Chiral auxiliary
Reversal of stereoselectivity

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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@article{7619345168b04d2992eba6fa8acafd56,

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

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.",

keywords = "Allylation, Chiral auxiliary, Reversal of stereoselectivity",

author = "Chen, {Jung Hsuan} and Uppala Venkatesham and Lee, {Li Chen} and Kwunmin Chen",

note = "Funding Information: This work was supported by the National Science Council of the Republic of China (NSC 94-2113-M-003-003) and the National Taiwan Normal University (ORD 93-C). The X-ray crystal data were collected and processed by National Taiwan Normal University are gratefully acknowledged. ",

year = "2006",

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doi = "10.1016/j.tet.2005.10.042",

language = "English",

volume = "62",

pages = "887--893",

journal = "Tetrahedron",

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T1 - Diastereoselective allylation of α-ketoamides bearing camphor N-tosylpyrazolidinone auxiliary

T2 - Efficient synthesis of highly optically active two stereoisomers

AU - Chen, Jung Hsuan

AU - Venkatesham, Uppala

AU - Lee, Li Chen

AU - Chen, Kwunmin

N1 - Funding Information: This work was supported by the National Science Council of the Republic of China (NSC 94-2113-M-003-003) and the National Taiwan Normal University (ORD 93-C). The X-ray crystal data were collected and processed by National Taiwan Normal University are gratefully acknowledged.

PY - 2006/1/30

Y1 - 2006/1/30

N2 - 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.

AB - 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.

KW - Allylation

KW - Chiral auxiliary

KW - Reversal of stereoselectivity

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