On Enantioselective Deprotonation: Synthesis and Crystal Structure of a Chiral Amidolithium Tetrahydrofuran Complex

Andrew J. Edwards; Susan Hockey; Francis S. Mair; Paul R. Raithby; Ronald Snaith; Nigel S. Simpkins

doi:10.1021/jo00077a002

On Enantioselective Deprotonation: Synthesis and Crystal Structure of a Chiral Amidolithium Tetrahydrofuran Complex

Andrew J. Edwards, Susan Hockey, Francis S. Mair, Paul R. Raithby, Ronald Snaith, Nigel S. Simpkins

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

Abstract

The enantioselective base (R,R′)-bis(1-phenylethyl)amidolithium (1) was crystallized from THF/hexane and characterized by X-ray crystallography as a bis-THF-solvated cyclic dimer which adopts a conformation that maximizes methyllithium contacts, inconsistent with previous rationalizations of its enantioselectivity in enolizations of cyclic ketones.

Original language	English
Pages (from-to)	6942-6943
Number of pages	2
Journal	Journal of Organic Chemistry
Volume	58
Issue number	25
DOIs	https://doi.org/10.1021/jo00077a002
Publication status	Published - 1993

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Organic Chemistry

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title = "On Enantioselective Deprotonation: Synthesis and Crystal Structure of a Chiral Amidolithium Tetrahydrofuran Complex",

abstract = "The enantioselective base (R,R′)-bis(1-phenylethyl)amidolithium (1) was crystallized from THF/hexane and characterized by X-ray crystallography as a bis-THF-solvated cyclic dimer which adopts a conformation that maximizes methyllithium contacts, inconsistent with previous rationalizations of its enantioselectivity in enolizations of cyclic ketones.",

author = "Edwards, {Andrew J.} and Susan Hockey and Mair, {Francis S.} and Raithby, {Paul R.} and Ronald Snaith and Simpkins, {Nigel S.}",

year = "1993",

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pages = "6942--6943",

journal = "Journal of Organic Chemistry",

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AU - Mair, Francis S.

AU - Raithby, Paul R.

AU - Snaith, Ronald

AU - Simpkins, Nigel S.

PY - 1993

Y1 - 1993

N2 - The enantioselective base (R,R′)-bis(1-phenylethyl)amidolithium (1) was crystallized from THF/hexane and characterized by X-ray crystallography as a bis-THF-solvated cyclic dimer which adopts a conformation that maximizes methyllithium contacts, inconsistent with previous rationalizations of its enantioselectivity in enolizations of cyclic ketones.

AB - The enantioselective base (R,R′)-bis(1-phenylethyl)amidolithium (1) was crystallized from THF/hexane and characterized by X-ray crystallography as a bis-THF-solvated cyclic dimer which adopts a conformation that maximizes methyllithium contacts, inconsistent with previous rationalizations of its enantioselectivity in enolizations of cyclic ketones.

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DO - 10.1021/jo00077a002

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AN - SCOPUS:0001744509

SN - 0022-3263

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

On Enantioselective Deprotonation: Synthesis and Crystal Structure of a Chiral Amidolithium Tetrahydrofuran Complex

Abstract

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