Enantioselective MSPV reduction of ketimines using 2-propanol and (BINOL)AlIII

Christopher R. Graves; Karl A. Scheidt; Son Binh T. Nguyen

doi:10.1021/ol060110w

Enantioselective MSPV reduction of ketimines using 2-propanol and (BINOL)Al^III

Christopher R. Graves, Karl A. Scheidt^*, Son Binh T. Nguyen

^*Corresponding author for this work

Chemistry

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

47 Scopus citations

Abstract

A highly enantioselective Meerwein-Schmidt-Ponndorf-Verley (MSPV) reduction of N-phosphinoyl ketimines by (BINOL)Al^III/2-propanol is reported. Yields ranging between 79 and 85% with high enantiomeric excesses (93-98%) are observed for a wide range of structurally diverse ketimines. A [2.0.4] bicyclic chelation model is proposed to account for this high selectivity.

Original language	English (US)
Pages (from-to)	1229-1232
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	6
DOIs	https://doi.org/10.1021/ol060110w
State	Published - Mar 16 2006

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol060110w

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title = "Enantioselective MSPV reduction of ketimines using 2-propanol and (BINOL)AlIII",

abstract = "A highly enantioselective Meerwein-Schmidt-Ponndorf-Verley (MSPV) reduction of N-phosphinoyl ketimines by (BINOL)AlIII/2-propanol is reported. Yields ranging between 79 and 85% with high enantiomeric excesses (93-98%) are observed for a wide range of structurally diverse ketimines. A [2.0.4] bicyclic chelation model is proposed to account for this high selectivity.",

author = "Graves, {Christopher R.} and Scheidt, {Karl A.} and Nguyen, {Son Binh T.}",

year = "2006",

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doi = "10.1021/ol060110w",

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journal = "Organic Letters",

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T1 - Enantioselective MSPV reduction of ketimines using 2-propanol and (BINOL)AlIII

AU - Graves, Christopher R.

AU - Scheidt, Karl A.

AU - Nguyen, Son Binh T.

PY - 2006/3/16

Y1 - 2006/3/16

N2 - A highly enantioselective Meerwein-Schmidt-Ponndorf-Verley (MSPV) reduction of N-phosphinoyl ketimines by (BINOL)AlIII/2-propanol is reported. Yields ranging between 79 and 85% with high enantiomeric excesses (93-98%) are observed for a wide range of structurally diverse ketimines. A [2.0.4] bicyclic chelation model is proposed to account for this high selectivity.

AB - A highly enantioselective Meerwein-Schmidt-Ponndorf-Verley (MSPV) reduction of N-phosphinoyl ketimines by (BINOL)AlIII/2-propanol is reported. Yields ranging between 79 and 85% with high enantiomeric excesses (93-98%) are observed for a wide range of structurally diverse ketimines. A [2.0.4] bicyclic chelation model is proposed to account for this high selectivity.

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JO - Organic Letters

JF - Organic Letters

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Enantioselective MSPV reduction of ketimines using 2-propanol and (BINOL)Al^III

Abstract

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