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 Canary

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)459-462
Number of pages4
JournalTetrahedron Letters
Volume57
Issue number4
DOIs
StatePublished - Jan 27 2016

Fingerprint

Catalysis
Oxidation-Reduction
Catalysts
Substrates
Instrument dials
Addition reactions
Stereochemistry
Oxidation

Keywords

  • Ambidextrous
  • Asymmetric catalysis
  • Dynamic
  • Helical inversion
  • Michael addition

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Dial-in selection of any of four stereochemical outcomes among two substrates by in situ stereo-reconfiguration of a single ambidextrous catalyst. / Mortezaei, Shahab; Catarineu, Noelle R.; Canary, James.

In: Tetrahedron Letters, Vol. 57, No. 4, 27.01.2016, p. 459-462.

Research output: Contribution to journalArticle

@article{63905dd9ba5b4f6aaa94485f433a746c,
title = "Dial-in selection of any of four stereochemical outcomes among two substrates by in situ stereo-reconfiguration of a single ambidextrous catalyst",
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.",
keywords = "Ambidextrous, Asymmetric catalysis, Dynamic, Helical inversion, Michael addition",
author = "Shahab Mortezaei and Catarineu, {Noelle R.} and James Canary",
year = "2016",
month = "1",
day = "27",
doi = "10.1016/j.tetlet.2015.12.015",
language = "English (US)",
volume = "57",
pages = "459--462",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "4",

}

TY - JOUR

T1 - Dial-in selection of any of four stereochemical outcomes among two substrates by in situ stereo-reconfiguration of a single ambidextrous catalyst

AU - Mortezaei, Shahab

AU - Catarineu, Noelle R.

AU - Canary, James

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

UR - http://www.scopus.com/inward/record.url?scp=84953287130&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84953287130&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2015.12.015

DO - 10.1016/j.tetlet.2015.12.015

M3 - Article

VL - 57

SP - 459

EP - 462

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 4

ER -