Chiral phosphoric acid-governed anti-diastereoselective and enantioselective Hetero-Diels - Alder reaction of glyoxylate

Norie Momiyama; Hideaki Tabuse; Masahiro Terada

doi:10.1021/ja904749x

Chiral phosphoric acid-governed anti-diastereoselective and enantioselective Hetero-Diels - Alder reaction of glyoxylate

Norie Momiyama, Hideaki Tabuse, Masahiro Terada

SCI - Chemistry

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

84 Citations (Scopus)

Abstract

(Chemical Equation Presented) A highly enantioselective anti-diastereoselective hetero-Diels-Alder reaction between a glyoxylate and siloxy- or methoxydienes using a chiral phosphoric acid catalyst that possesses less bulky phenyl groups at the 3 and 3′ positions of binaphthyl has been developed. The diastereoselectivities presented are disparate to those previously reported for hetero-Diels-Alder reactions catalyzed by a chiral Lewis acid.

Original language	English
Pages (from-to)	12882-12883
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	131
Issue number	36
DOIs	https://doi.org/10.1021/ja904749x
Publication status	Published - 2009 Sept 16

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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abstract = "(Chemical Equation Presented) A highly enantioselective anti-diastereoselective hetero-Diels-Alder reaction between a glyoxylate and siloxy- or methoxydienes using a chiral phosphoric acid catalyst that possesses less bulky phenyl groups at the 3 and 3′ positions of binaphthyl has been developed. The diastereoselectivities presented are disparate to those previously reported for hetero-Diels-Alder reactions catalyzed by a chiral Lewis acid.",

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AU - Terada, Masahiro

PY - 2009/9/16

Y1 - 2009/9/16

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AB - (Chemical Equation Presented) A highly enantioselective anti-diastereoselective hetero-Diels-Alder reaction between a glyoxylate and siloxy- or methoxydienes using a chiral phosphoric acid catalyst that possesses less bulky phenyl groups at the 3 and 3′ positions of binaphthyl has been developed. The diastereoselectivities presented are disparate to those previously reported for hetero-Diels-Alder reactions catalyzed by a chiral Lewis acid.

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Chiral phosphoric acid-governed anti-diastereoselective and enantioselective Hetero-Diels - Alder reaction of glyoxylate

Abstract

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