Direct organocatalytic Mannich reaction of acetaldehyde: An improved catalyst and mechanistic insight from a computational study

Yujiro Hayashi; Tsubasa Okano; Takahiko Itoh; Tatsuya Urushima; Hayato Ishikawa; Tadafumi Uchimaru

doi:10.1002/anie.200802073

Direct organocatalytic Mannich reaction of acetaldehyde: An improved catalyst and mechanistic insight from a computational study

Yujiro Hayashi, Tsubasa Okano, Takahiko Itoh, Tatsuya Urushima, Hayato Ishikawa, Tadafumi Uchimaru

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

100 Citations (Scopus)

Abstract

(Chemical Equation Presented) A chiral diaryl prolinol silyl ether organocatalyst with an acidis used for the direct catalytic asymmetric Mannich reaction of acetaldehyde and imines. N-Benzoyl-, N-tert-butoxycarbonyl-, and N-toluene-4-sulfonylimines can be employed to produce synthetically useful β-amino aldehydes in goodyield s andwith excellent enantioselectivity (see scheme). The reaction mechanism was investigated quantum-mechanically.

Original language	English
Pages (from-to)	9053-9058
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	47
DOIs	https://doi.org/10.1002/anie.200802073
Publication status	Published - 2008 Nov 10
Externally published	Yes

Keywords

Acetaldehyde
Asymmetric catalysis
Imines
Mannich reactions
Organocatalysis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200802073

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Direct organocatalytic Mannich reaction of acetaldehyde : An improved catalyst and mechanistic insight from a computational study. / Hayashi, Yujiro; Okano, Tsubasa; Itoh, Takahiko; Urushima, Tatsuya; Ishikawa, Hayato; Uchimaru, Tadafumi.

In: Angewandte Chemie - International Edition, Vol. 47, No. 47, 10.11.2008, p. 9053-9058.

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

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AU - Urushima, Tatsuya

AU - Ishikawa, Hayato

AU - Uchimaru, Tadafumi

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KW - Imines

KW - Mannich reactions

KW - Organocatalysis

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Direct organocatalytic Mannich reaction of acetaldehyde: An improved catalyst and mechanistic insight from a computational study

Abstract

Keywords

ASJC Scopus subject areas

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