Lithium diisopinocampheylamide: A new and highly effective chiral catalyst in the enantioselective deprotonation of meso-epoxides

Sanjay V. Malhotra

doi:10.1016/S0957-4166(03)00080-6

Lithium diisopinocampheylamide: A new and highly effective chiral catalyst in the enantioselective deprotonation of meso-epoxides

Sanjay V. Malhotra

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

22 Scopus citations

Abstract

α-Pinene based novel chiral lithium amides have been used for the catalytic enantioselective deprotonation of cyclohexene oxide. An enantiomeric excess of up to 95% for (R)-2-scyclohexen-1-ol was achieved with lithium (-)-N,N-diisopinocampheylamide. A systematic study shows that the isopinocampheyl moiety plays an important role in achieving high enantioselectivity.

Original language	English (US)
Pages (from-to)	645-647
Number of pages	3
Journal	Tetrahedron Asymmetry
Volume	14
Issue number	6
DOIs	https://doi.org/10.1016/S0957-4166(03)00080-6
State	Published - Mar 21 2003
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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abstract = "α-Pinene based novel chiral lithium amides have been used for the catalytic enantioselective deprotonation of cyclohexene oxide. An enantiomeric excess of up to 95% for (R)-2-scyclohexen-1-ol was achieved with lithium (-)-N,N-diisopinocampheylamide. A systematic study shows that the isopinocampheyl moiety plays an important role in achieving high enantioselectivity.",

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N2 - α-Pinene based novel chiral lithium amides have been used for the catalytic enantioselective deprotonation of cyclohexene oxide. An enantiomeric excess of up to 95% for (R)-2-scyclohexen-1-ol was achieved with lithium (-)-N,N-diisopinocampheylamide. A systematic study shows that the isopinocampheyl moiety plays an important role in achieving high enantioselectivity.

AB - α-Pinene based novel chiral lithium amides have been used for the catalytic enantioselective deprotonation of cyclohexene oxide. An enantiomeric excess of up to 95% for (R)-2-scyclohexen-1-ol was achieved with lithium (-)-N,N-diisopinocampheylamide. A systematic study shows that the isopinocampheyl moiety plays an important role in achieving high enantioselectivity.

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Lithium diisopinocampheylamide: A new and highly effective chiral catalyst in the enantioselective deprotonation of meso-epoxides

Abstract

ASJC Scopus subject areas

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