Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation.

Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation. Research Abstract Details 

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Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation. Abstract Text:

Daisuke Uraguchi,Masahiro Terada,

It was found that the phosphoric acid derivatives of general structure 1 serve as highly effective catalysts for the direct addition of acetyl acetone to N-Boc-protected arylimines. The beneficial effects of the 3,3'-bisaryl substituents of the catalysts on the enantioselectivity are greatly appreciated, and thus 1d functions as an excellent catalyst. The Brønsted acid-catalyzed direct Mannich reactions presented herein provide an attractive way to construct beta-aminoketones under extremely mild conditions. The stereochemical course of this reaction was established through the synthesis of Boc-(S)-phenylglycine methylester. The transformation thus demonstrated is applicable to a useful method for the synthesis of various phenylglycine derivatives.

Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation. Publishing Authors By Initials

D Uraguchi,M Terada,

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Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Journal of the American Chemical Society

VOLUME: 126

Page Numbers: 5356-7

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 5

MONTH: May

YEAR: 2004

Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation. Information

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LANGUAGE: eng

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Grant and Affiliation Information for Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation.

AFFILIATION: Graduate School of Science, Department of Chemistry, Tohoku University, Sendai 980-8578, Japan.

Country: United States

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MEDLINETA: J Am Chem Soc

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