Anti-selective direct catalytic asymmetric aldol reaction of thiolactams

Devarajulu Sureshkumar; Yuji Kawato; Mitsutaka Iwata; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1021/ol301200q

Anti-selective direct catalytic asymmetric aldol reaction of thiolactams

Devarajulu Sureshkumar, Yuji Kawato, Mitsutaka Iwata, Naoya Kumagai, Masakatsu Shibasaki

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

22 Citations (Scopus)

Abstract

An anti-selective direct catalytic asymmetric aldol reaction of thiolactam is described. A soft Lewis acid/hard Brønsted base cooperative catalyst comprised of mesitylcopper/(R,R)-Ph-BPE exhibited high catalytic performance to produce an anti-aldol product with high stereoselectivity. The highly chemoselective nature of the present catalysis allows for the use of enolizable aldehydes as aldol acceptors. The diverse transformations of the thiolactam moiety highlight the synthetic utility of the present anti-aldol protocol.

Original language	English
Pages (from-to)	3108-3111
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	12
DOIs	https://doi.org/10.1021/ol301200q
Publication status	Published - 2012 Jun 15
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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author = "Devarajulu Sureshkumar and Yuji Kawato and Mitsutaka Iwata and Naoya Kumagai and Masakatsu Shibasaki",

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T1 - Anti-selective direct catalytic asymmetric aldol reaction of thiolactams

AU - Sureshkumar, Devarajulu

AU - Kawato, Yuji

AU - Iwata, Mitsutaka

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2012/6/15

Y1 - 2012/6/15

N2 - An anti-selective direct catalytic asymmetric aldol reaction of thiolactam is described. A soft Lewis acid/hard Brønsted base cooperative catalyst comprised of mesitylcopper/(R,R)-Ph-BPE exhibited high catalytic performance to produce an anti-aldol product with high stereoselectivity. The highly chemoselective nature of the present catalysis allows for the use of enolizable aldehydes as aldol acceptors. The diverse transformations of the thiolactam moiety highlight the synthetic utility of the present anti-aldol protocol.

AB - An anti-selective direct catalytic asymmetric aldol reaction of thiolactam is described. A soft Lewis acid/hard Brønsted base cooperative catalyst comprised of mesitylcopper/(R,R)-Ph-BPE exhibited high catalytic performance to produce an anti-aldol product with high stereoselectivity. The highly chemoselective nature of the present catalysis allows for the use of enolizable aldehydes as aldol acceptors. The diverse transformations of the thiolactam moiety highlight the synthetic utility of the present anti-aldol protocol.

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JO - Organic Letters

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Anti-selective direct catalytic asymmetric aldol reaction of thiolactams

Abstract

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