The preparation of nonracemic secondary alpha-(carbamoyloxy)alkylzinc and copper reagents. A versatile approach to enantioenriched alcohols

J P N  Papillon; R J K  Taylor

doi:10.1021/ol016986e

The preparation of nonracemic secondary alpha-(carbamoyloxy)alkylzinc and copper reagents. A versatile approach to enantioenriched alcohols

J P N Papillon, R J K Taylor

Chemistry

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

Abstract

GRAPHICS

Chiral alpha-(carbamoyloxy)alkyllithium reagents, prepared using Hoppe's sBuLi/(-)-sparteine methodology, were transmetalated with ZnCl2. Further transmetalation with CuCN with overall retention of configuration gave chiral species that reacted with various electrophiles to give enantiomerically pure alcohols after deprotection. A short, highly efficient synthesis of an industrially relevant pheromone, japonilure, illustrates the value of the methodology.

Original language	English
Pages (from-to)	119-122
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	1
DOIs	https://doi.org/10.1021/ol016986e
Publication status	Published - 10 Jan 2002

Keywords

BENZYLIC ORGANOZINC HALIDES
JAPANESE-BEETLE
SEX-PHEROMONE
INTRAMOLECULAR CARBOLITHIATION
ENANTIOSELECTIVE SYNTHESIS
CONFIGURATIONAL STABILITY
STEREOSPECIFIC SYNTHESIS
ORGANIC-SYNTHESIS
ACYL CHLORIDES
VINYL ETHERS

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10.1021/ol016986e

Cite this

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title = "The preparation of nonracemic secondary alpha-(carbamoyloxy)alkylzinc and copper reagents. A versatile approach to enantioenriched alcohols",

abstract = "GRAPHICSChiral alpha-(carbamoyloxy)alkyllithium reagents, prepared using Hoppe's sBuLi/(-)-sparteine methodology, were transmetalated with ZnCl2. Further transmetalation with CuCN with overall retention of configuration gave chiral species that reacted with various electrophiles to give enantiomerically pure alcohols after deprotection. A short, highly efficient synthesis of an industrially relevant pheromone, japonilure, illustrates the value of the methodology.",

keywords = "BENZYLIC ORGANOZINC HALIDES, JAPANESE-BEETLE, SEX-PHEROMONE, INTRAMOLECULAR CARBOLITHIATION, ENANTIOSELECTIVE SYNTHESIS, CONFIGURATIONAL STABILITY, STEREOSPECIFIC SYNTHESIS, ORGANIC-SYNTHESIS, ACYL CHLORIDES, VINYL ETHERS",

author = "Papillon, {J P N} and Taylor, {R J K}",

year = "2002",

month = jan,

day = "10",

doi = "10.1021/ol016986e",

language = "English",

volume = "4",

pages = "119--122",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - The preparation of nonracemic secondary alpha-(carbamoyloxy)alkylzinc and copper reagents. A versatile approach to enantioenriched alcohols

AU - Papillon, J P N

AU - Taylor, R J K

PY - 2002/1/10

Y1 - 2002/1/10

N2 - GRAPHICSChiral alpha-(carbamoyloxy)alkyllithium reagents, prepared using Hoppe's sBuLi/(-)-sparteine methodology, were transmetalated with ZnCl2. Further transmetalation with CuCN with overall retention of configuration gave chiral species that reacted with various electrophiles to give enantiomerically pure alcohols after deprotection. A short, highly efficient synthesis of an industrially relevant pheromone, japonilure, illustrates the value of the methodology.

AB - GRAPHICSChiral alpha-(carbamoyloxy)alkyllithium reagents, prepared using Hoppe's sBuLi/(-)-sparteine methodology, were transmetalated with ZnCl2. Further transmetalation with CuCN with overall retention of configuration gave chiral species that reacted with various electrophiles to give enantiomerically pure alcohols after deprotection. A short, highly efficient synthesis of an industrially relevant pheromone, japonilure, illustrates the value of the methodology.

KW - BENZYLIC ORGANOZINC HALIDES

KW - JAPANESE-BEETLE

KW - SEX-PHEROMONE

KW - INTRAMOLECULAR CARBOLITHIATION

KW - ENANTIOSELECTIVE SYNTHESIS

KW - CONFIGURATIONAL STABILITY

KW - STEREOSPECIFIC SYNTHESIS

KW - ORGANIC-SYNTHESIS

KW - ACYL CHLORIDES

KW - VINYL ETHERS

U2 - 10.1021/ol016986e

DO - 10.1021/ol016986e

M3 - Article

SN - 1523-7060

VL - 4

SP - 119

EP - 122

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -