Generation of allylic and benzylic organolithium reagents from the corresponding ester, amide, carbonate, carbamate and urea derivatives | Health & Environmental Research Online (HERO)

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Citation
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HERO ID

7442831

Reference Type

Journal Article

Title

Generation of allylic and benzylic organolithium reagents from the corresponding ester, amide, carbonate, carbamate and urea derivatives

Author(s)

Alonso, E; Guijarro, D; Martinez, P; Ramon, DJ; Yus, M

Year

1999

Is Peer Reviewed?

Journal

Tetrahedron
ISSN: 0040-4020

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

Location

OXFORD

Volume

Issue

Page Numbers

11027-11038

Language

English

DOI

10.1016/S0040-4020(99)00610-9

Web of Science Id

WOS:000082200000014

URL

https://linkinghub.elsevier.com/retrieve/pii/S0040402099006109
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Abstract

The reaction of different allylic and benzylic non-enolisable esters or amides (1), carbonates (4), carbamates (6, 7) and ureas (8) with an excess of lithium powder and a catalytic amount of naphthalene (10%) in the presence of an electrophile [iPrCHO, tBuCHO, PhCHO, Me2CO, Et2CO, (CH2)(5)CO, Ph2CO, MeSiCl] in THF at different temperatures (-78, -30 or 0 degrees C) leads, after hydrolysis with water, to the corresponding allylated or benzylated products (2). (C) 1999 Elsevier Science Ltd. All rights reserved.

Keywords

lithiation; catalysis; lithium and compounds; allylation; benzylation