Diastereoselective Baylis-Hillman reactions: The design and synthesis of a novel camphor-Based chiral auxiliary

Kung Shuo Yang; Kwunmin Chen

doi:10.1021/ol990315n

Diastereoselective Baylis-Hillman reactions: The design and synthesis of a novel camphor-Based chiral auxiliary

Kung Shuo Yang, Kwunmin Chen^*

^*Corresponding author for this work

Department of Chemistry

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

112 Citations (Scopus)

Abstract

Formula presented Reaction of chiral acryloylhydrazide 5 derived from novel auxiliary 4 with aldehydes in the presence of DABCO affords practical levels (up to 98% de) of β-hydroxy-α-methylene carbonyl derivatives, and high optical purity of both diastereomers of 6a-d and 7a-d can be obtained by changing the solvent.

Original language	English
Pages (from-to)	729-731
Number of pages	3
Journal	Organic Letters
Volume	2
Issue number	6
DOIs	https://doi.org/10.1021/ol990315n
Publication status	Published - 2000 Mar 23

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol990315n

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title = "Diastereoselective Baylis-Hillman reactions: The design and synthesis of a novel camphor-Based chiral auxiliary",

abstract = "Formula presented Reaction of chiral acryloylhydrazide 5 derived from novel auxiliary 4 with aldehydes in the presence of DABCO affords practical levels (up to 98% de) of β-hydroxy-α-methylene carbonyl derivatives, and high optical purity of both diastereomers of 6a-d and 7a-d can be obtained by changing the solvent.",

author = "Yang, {Kung Shuo} and Kwunmin Chen",

year = "2000",

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doi = "10.1021/ol990315n",

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AU - Yang, Kung Shuo

AU - Chen, Kwunmin

PY - 2000/3/23

Y1 - 2000/3/23

N2 - Formula presented Reaction of chiral acryloylhydrazide 5 derived from novel auxiliary 4 with aldehydes in the presence of DABCO affords practical levels (up to 98% de) of β-hydroxy-α-methylene carbonyl derivatives, and high optical purity of both diastereomers of 6a-d and 7a-d can be obtained by changing the solvent.

AB - Formula presented Reaction of chiral acryloylhydrazide 5 derived from novel auxiliary 4 with aldehydes in the presence of DABCO affords practical levels (up to 98% de) of β-hydroxy-α-methylene carbonyl derivatives, and high optical purity of both diastereomers of 6a-d and 7a-d can be obtained by changing the solvent.

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Diastereoselective Baylis-Hillman reactions: The design and synthesis of a novel camphor-Based chiral auxiliary

Abstract

ASJC Scopus subject areas

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