Carbamate-directed benzylic lithiation for the diastereo- and enantioselective synthesis of diaryl ether atropisomers

Abigail Page; Jonathan Clayden

doi:10.3762/bjoc.7.156

Carbamate-directed benzylic lithiation for the diastereo- and enantioselective synthesis of diaryl ether atropisomers

Abigail Page, Jonathan Clayden

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

Abstract

Diaryl ethers carrying carbamoyloxymethyl groups may be desymmetrised enantio- and diastereoselectively by the use of the sec-BuLi-(-)-sparteine complex in diethyl ether. Enantioselective deprotonation of one of the two benzylic positions leads to atropisomeric products with ca. 80:20 e.r.; an electrophilic quench typically provides functionalised atropisomeric diastereoisomers in up to 97:3 d.r. © 2011 Page and Clayden; licensee Beilstein-Institut.

Original language	English
Pages (from-to)	1327-1333
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	7
DOIs	https://doi.org/10.3762/bjoc.7.156
Publication status	Published - 23 Sept 2011

Keywords

Configurational stability
Diaryl ether
Diastereoselective
Enantioselective
Lateral lithiation
Metallation

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10.3762/bjoc.7.156

http://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-7-156.pdf

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title = "Carbamate-directed benzylic lithiation for the diastereo- and enantioselective synthesis of diaryl ether atropisomers",

abstract = "Diaryl ethers carrying carbamoyloxymethyl groups may be desymmetrised enantio- and diastereoselectively by the use of the sec-BuLi-(-)-sparteine complex in diethyl ether. Enantioselective deprotonation of one of the two benzylic positions leads to atropisomeric products with ca. 80:20 e.r.; an electrophilic quench typically provides functionalised atropisomeric diastereoisomers in up to 97:3 d.r. {\textcopyright} 2011 Page and Clayden; licensee Beilstein-Institut.",

keywords = "Configurational stability, Diaryl ether, Diastereoselective, Enantioselective, Lateral lithiation, Metallation",

author = "Abigail Page and Jonathan Clayden",

year = "2011",

month = sep,

day = "23",

doi = "10.3762/bjoc.7.156",

language = "English",

volume = "7",

pages = "1327--1333",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

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T1 - Carbamate-directed benzylic lithiation for the diastereo- and enantioselective synthesis of diaryl ether atropisomers

AU - Page, Abigail

AU - Clayden, Jonathan

PY - 2011/9/23

Y1 - 2011/9/23

N2 - Diaryl ethers carrying carbamoyloxymethyl groups may be desymmetrised enantio- and diastereoselectively by the use of the sec-BuLi-(-)-sparteine complex in diethyl ether. Enantioselective deprotonation of one of the two benzylic positions leads to atropisomeric products with ca. 80:20 e.r.; an electrophilic quench typically provides functionalised atropisomeric diastereoisomers in up to 97:3 d.r. © 2011 Page and Clayden; licensee Beilstein-Institut.

AB - Diaryl ethers carrying carbamoyloxymethyl groups may be desymmetrised enantio- and diastereoselectively by the use of the sec-BuLi-(-)-sparteine complex in diethyl ether. Enantioselective deprotonation of one of the two benzylic positions leads to atropisomeric products with ca. 80:20 e.r.; an electrophilic quench typically provides functionalised atropisomeric diastereoisomers in up to 97:3 d.r. © 2011 Page and Clayden; licensee Beilstein-Institut.

KW - Configurational stability

KW - Diaryl ether

KW - Diastereoselective

KW - Enantioselective

KW - Lateral lithiation

KW - Metallation

U2 - 10.3762/bjoc.7.156

DO - 10.3762/bjoc.7.156

M3 - Article

SN - 1860-5397

VL - 7

SP - 1327

EP - 1333

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Carbamate-directed benzylic lithiation for the diastereo- and enantioselective synthesis of diaryl ether atropisomers

Abstract

Keywords

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