An alkylidene carbene C-H insertion strategy for the enantioselective synthesis of alpha,alpha-dialkyl-alpha-amino acids

Authors
Gabaitsekgosi, R Hayes, CJ
Citation
R. Gabaitsekgosi et Cj. Hayes, An alkylidene carbene C-H insertion strategy for the enantioselective synthesis of alpha,alpha-dialkyl-alpha-amino acids, TETRAHEDR L, 40(43), 1999, pp. 7713-7716
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
43
Year of publication
1999
Pages
7713 - 7716
Database
ISI
SICI code
0040-4039(19991022)40:43<7713:AACCIS>2.0.ZU;2-3
Abstract
A synthesis of the alpha,alpha-dialkyl-alpha-amino acid (1S,3R)-2,5-methano -leucine has been achieved using an alkylidene carbene 1,5-C-H insertion re action as a key step. Treatment of the ketone 11 with 1.2 equivalents of li thio(trimethylsilyl)diazomethane in THF resulted in the formation of the cy clopentene 13 in 62% yield. The enantiomeric excess of the product 18 was d etermined to be >95% by chiral HPLC (Chiracel OD column). (C) 1999 Elsevier Science Ltd. All rights reserved.