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

University of Cambridge
University of Nottingham

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

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo00077a002

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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.",

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year = "1993",

doi = "10.1021/jo00077a002",

language = "English",

volume = "58",

pages = "6942--6943",

journal = "Journal of Organic Chemistry",

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publisher = "American Chemical Society",

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T2 - Synthesis and Crystal Structure of a Chiral Amidolithium Tetrahydrofuran Complex

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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.

UR - https://www.scopus.com/pages/publications/0001744509

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DO - 10.1021/jo00077a002

M3 - Article

AN - SCOPUS:0001744509

SN - 0022-3263

VL - 58

SP - 6942

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 25

ER -

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

Abstract

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