Dial-in selection of any of four stereochemical outcomes among two substrates by in situ stereo-reconfiguration of a single ambidextrous catalyst

Shahab Mortezaei; Noelle R. Catarineu; James W. Canary

doi:10.1016/j.tetlet.2015.12.015

Dial-in selection of any of four stereochemical outcomes among two substrates by in situ stereo-reconfiguration of a single ambidextrous catalyst

Shahab Mortezaei, Noelle R. Catarineu, James W. Canary

Chemistry

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

Abstract

We provide proof-of-principle that an ambidextrous catalyst is capable of independent, dial-in control of the absolute stereochemistry of two similar nitrostyrene Michael addition reactions by in situ oxidation and reduction of the catalyst. The catalyst is capable of both static and dynamic catalysis modes; in combination both modes allow access to all four possible stereochemical outcomes for the two nitroalkane products in a single process.

Original language	English (US)
Pages (from-to)	459-462
Number of pages	4
Journal	Tetrahedron Letters
Volume	57
Issue number	4
DOIs	https://doi.org/10.1016/j.tetlet.2015.12.015
State	Published - Jan 27 2016

Keywords

Ambidextrous
Asymmetric catalysis
Dynamic
Helical inversion
Michael addition

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2015.12.015

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abstract = "We provide proof-of-principle that an ambidextrous catalyst is capable of independent, dial-in control of the absolute stereochemistry of two similar nitrostyrene Michael addition reactions by in situ oxidation and reduction of the catalyst. The catalyst is capable of both static and dynamic catalysis modes; in combination both modes allow access to all four possible stereochemical outcomes for the two nitroalkane products in a single process.",

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AU - Mortezaei, Shahab

AU - Catarineu, Noelle R.

AU - Canary, James W.

PY - 2016/1/27

Y1 - 2016/1/27

N2 - We provide proof-of-principle that an ambidextrous catalyst is capable of independent, dial-in control of the absolute stereochemistry of two similar nitrostyrene Michael addition reactions by in situ oxidation and reduction of the catalyst. The catalyst is capable of both static and dynamic catalysis modes; in combination both modes allow access to all four possible stereochemical outcomes for the two nitroalkane products in a single process.

AB - We provide proof-of-principle that an ambidextrous catalyst is capable of independent, dial-in control of the absolute stereochemistry of two similar nitrostyrene Michael addition reactions by in situ oxidation and reduction of the catalyst. The catalyst is capable of both static and dynamic catalysis modes; in combination both modes allow access to all four possible stereochemical outcomes for the two nitroalkane products in a single process.

KW - Ambidextrous

KW - Asymmetric catalysis

KW - Dynamic

KW - Helical inversion

KW - Michael addition

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 4

ER -

Dial-in selection of any of four stereochemical outcomes among two substrates by in situ stereo-reconfiguration of a single ambidextrous catalyst

Abstract

Keywords

ASJC Scopus subject areas

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