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Synthesis of 2,3,4-Trisubstituted Thiochromanes using an Organocatalytic Enantioselective Tandem Michael-Henry Reaction.

ABSTRACT: Enantioenriched 2,3,4-trisubstituted thiochromanes have been synthesized by using a cupreine-catalyzed tandem Michael addition-Henry reaction between 2-mercaptobenzaldehydes and ?-nitrostyrenes. Good diastereoselectivities and enantioselectivities were obtained for the title compounds, which may be further improved through a single recrystallization (up to 98% de and> 99% ee).

SUBMITTER: Dodda R

PROVIDER: S-EPMC2760986 | biostudies-literature | 2008 Feb

REPOSITORIES: biostudies-literature

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Synthesis of 2,3,4-Trisubstituted Thiochromanes using an Organocatalytic Enantioselective Tandem Michael-Henry Reaction.

Dodda Rajasekhar R Goldman Joshua J JJ Mandal Tanmay T Zhao Cong-Gui CG Broker Grant A GA Tiekink Edward R T ER

Advanced synthesis & catalysis 20080201 4

Enantioenriched 2,3,4-trisubstituted thiochromanes have been synthesized by using a cupreine-catalyzed tandem Michael addition-Henry reaction between 2-mercaptobenzaldehydes and β-nitrostyrenes. Good diastereoselectivities and enantioselectivities were obtained for the title compounds, which may be further improved through a single recrystallization (up to 98% de and> 99% ee). ...[more]

PMID: 19829750

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