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

研究成果: Article › 査読

21 被引用数 (Scopus)

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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.

本文言語	English
ページ（範囲）	3108-3111
ページ数	4
ジャーナル	Organic Letters
巻	14
号	12
DOI	https://doi.org/10.1021/ol301200q
出版ステータス	Published - 2012 6月 15
外部発表	はい

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/ol301200q

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

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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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Anti-selective direct catalytic asymmetric aldol reaction of thiolactams

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