Auxiliary-Based, Asymmetric SN2' Reactions: A Case of 1,7-Relative Stereogenesis

Scott E. Denmark; Lyndon K. Marble

doi:10.1021/jo00294a006

Auxiliary-Based, Asymmetric SN2' Reactions: A Case of 1,7-Relative Stereogenesis

Scott E. Denmark, Lyndon K. Marble

Chemistry

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

Abstract

The asymmetric SN2' substitution of chiral carbamates derived from an achiral allylic alcohol has been developed. Using optically active amines as auxiliaries, the reaction has been optimized to give up to 92% ee with an SN2'/SN2 ratio of >100:1 with various copper reagents.

Original language	English (US)
Pages (from-to)	1984-1986
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	55
Issue number	7
DOIs	https://doi.org/10.1021/jo00294a006
State	Published - 1990

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Organic Chemistry

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10.1021/jo00294a006

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abstract = "The asymmetric SN2' substitution of chiral carbamates derived from an achiral allylic alcohol has been developed. Using optically active amines as auxiliaries, the reaction has been optimized to give up to 92% ee with an SN2'/SN2 ratio of >100:1 with various copper reagents.",

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N2 - The asymmetric SN2' substitution of chiral carbamates derived from an achiral allylic alcohol has been developed. Using optically active amines as auxiliaries, the reaction has been optimized to give up to 92% ee with an SN2'/SN2 ratio of >100:1 with various copper reagents.

AB - The asymmetric SN2' substitution of chiral carbamates derived from an achiral allylic alcohol has been developed. Using optically active amines as auxiliaries, the reaction has been optimized to give up to 92% ee with an SN2'/SN2 ratio of >100:1 with various copper reagents.

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SP - 1984

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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Auxiliary-Based, Asymmetric SN2' Reactions: A Case of 1,7-Relative Stereogenesis

Abstract

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