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

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

16 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1327-1333
Number of pages	7
Journal	Beilstein Journal of Organic Chemistry
Volume	7
DOIs	https://doi.org/10.3762/bjoc.7.156
Publication status	Published - 26 Sept 2011

Keywords

Configurational stability
Diaryl ether
Diastereoselective
Enantioselective
Lateral lithiation
Metallation

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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.",

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

author = "Abigail Page and Jonathan Clayden",

year = "2011",

month = sep,

day = "26",

doi = "10.3762/bjoc.7.156",

language = "English",

volume = "7",

pages = "1327--1333",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

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TY - JOUR

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

AU - Page, Abigail

AU - Clayden, Jonathan

PY - 2011/9/26

Y1 - 2011/9/26

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.

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.

KW - Configurational stability

KW - Diaryl ether

KW - Diastereoselective

KW - Enantioselective

KW - Lateral lithiation

KW - Metallation

UR - http://www.scopus.com/inward/record.url?scp=80053484036&partnerID=8YFLogxK

U2 - 10.3762/bjoc.7.156

DO - 10.3762/bjoc.7.156

M3 - Article (Academic Journal)

C2 - 22043243

AN - SCOPUS:80053484036

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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