Catalytic Meerwein-Pondorf-Verley reduction by simple aluminum complexes

E. Joseph Campbell; Hongying Zhou; Son Binh T. Nguyen

doi:10.1021/ol0162116

Catalytic Meerwein-Pondorf-Verley reduction by simple aluminum complexes

E. Joseph Campbell, Hongying Zhou, Son Binh T. Nguyen^*

^*Corresponding author for this work

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

117 Scopus citations

Abstract

(matrix presented) Catalytic MPV reduction was successfully carried out using simple aluminum precatalysts. Alkylaluminum reagents were converted to a low-aggregation aluminum alkoxide that was highly active for the MPV reduction of several carbonyl substrates in high yield (50-99%) using ⁱPrOH as the reducing agent. A high degree of cisftrans selectivity was achieved in the reduction of 2-methylcyclohexanone (cis/trans = 20/80) by ⁱPrOH. When chiral hydride sources were utilized in the reduction of 2-chloroacetophenone, high enantioselectivity (68-80% ee) was observed.

Original language	English (US)
Pages (from-to)	2391-2393
Number of pages	3
Journal	Organic Letters
Volume	3
Issue number	15
DOIs	https://doi.org/10.1021/ol0162116
State	Published - Jul 26 2001

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0162116

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title = "Catalytic Meerwein-Pondorf-Verley reduction by simple aluminum complexes",

abstract = "(matrix presented) Catalytic MPV reduction was successfully carried out using simple aluminum precatalysts. Alkylaluminum reagents were converted to a low-aggregation aluminum alkoxide that was highly active for the MPV reduction of several carbonyl substrates in high yield (50-99%) using iPrOH as the reducing agent. A high degree of cisftrans selectivity was achieved in the reduction of 2-methylcyclohexanone (cis/trans = 20/80) by iPrOH. When chiral hydride sources were utilized in the reduction of 2-chloroacetophenone, high enantioselectivity (68-80% ee) was observed.",

author = "Campbell, {E. Joseph} and Hongying Zhou and Nguyen, {Son Binh T.}",

year = "2001",

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doi = "10.1021/ol0162116",

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AU - Zhou, Hongying

AU - Nguyen, Son Binh T.

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N2 - (matrix presented) Catalytic MPV reduction was successfully carried out using simple aluminum precatalysts. Alkylaluminum reagents were converted to a low-aggregation aluminum alkoxide that was highly active for the MPV reduction of several carbonyl substrates in high yield (50-99%) using iPrOH as the reducing agent. A high degree of cisftrans selectivity was achieved in the reduction of 2-methylcyclohexanone (cis/trans = 20/80) by iPrOH. When chiral hydride sources were utilized in the reduction of 2-chloroacetophenone, high enantioselectivity (68-80% ee) was observed.

AB - (matrix presented) Catalytic MPV reduction was successfully carried out using simple aluminum precatalysts. Alkylaluminum reagents were converted to a low-aggregation aluminum alkoxide that was highly active for the MPV reduction of several carbonyl substrates in high yield (50-99%) using iPrOH as the reducing agent. A high degree of cisftrans selectivity was achieved in the reduction of 2-methylcyclohexanone (cis/trans = 20/80) by iPrOH. When chiral hydride sources were utilized in the reduction of 2-chloroacetophenone, high enantioselectivity (68-80% ee) was observed.

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Catalytic Meerwein-Pondorf-Verley reduction by simple aluminum complexes

Abstract

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