Enantioselective Diels-Alder reaction of α-(acylthio)acroleins: A new entry to sulfur-containing chiral quaternary carbons

Akira Sakakura; Hiroki Yamada; Kazuaki Ishihara

doi:10.1021/ol300921f

Enantioselective Diels-Alder reaction of α-(acylthio)acroleins: A new entry to sulfur-containing chiral quaternary carbons

Akira Sakakura, Hiroki Yamada, Kazuaki Ishihara

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

25 Citations (Scopus)

Abstract

A catalytic and enantioselective Diels-Alder reaction of α-(carbamoylthio)acroleins induced by an organoammonium salt of chiral triamine is described. α-(Carbamoylthio)acroleins are designed and synthesized as new sulfur-containing dienophiles for the first time. The Diels-Alder reaction affords chiral tertiary thiol precursors with up to 91% ee.

Original language	English
Pages (from-to)	2972-2975
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	12
DOIs	https://doi.org/10.1021/ol300921f
Publication status	Published - Jun 15 2012
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A catalytic and enantioselective Diels-Alder reaction of α-(carbamoylthio)acroleins induced by an organoammonium salt of chiral triamine is described. α-(Carbamoylthio)acroleins are designed and synthesized as new sulfur-containing dienophiles for the first time. The Diels-Alder reaction affords chiral tertiary thiol precursors with up to 91% ee.",

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T2 - A new entry to sulfur-containing chiral quaternary carbons

AU - Sakakura, Akira

AU - Yamada, Hiroki

AU - Ishihara, Kazuaki

PY - 2012/6/15

Y1 - 2012/6/15

N2 - A catalytic and enantioselective Diels-Alder reaction of α-(carbamoylthio)acroleins induced by an organoammonium salt of chiral triamine is described. α-(Carbamoylthio)acroleins are designed and synthesized as new sulfur-containing dienophiles for the first time. The Diels-Alder reaction affords chiral tertiary thiol precursors with up to 91% ee.

AB - A catalytic and enantioselective Diels-Alder reaction of α-(carbamoylthio)acroleins induced by an organoammonium salt of chiral triamine is described. α-(Carbamoylthio)acroleins are designed and synthesized as new sulfur-containing dienophiles for the first time. The Diels-Alder reaction affords chiral tertiary thiol precursors with up to 91% ee.

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Enantioselective Diels-Alder reaction of α-(acylthio)acroleins: A new entry to sulfur-containing chiral quaternary carbons

Abstract

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