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Titolo:
alpha-aminated methyllithium by DTBB-catalysed lithiation of a N-(chloromethyl)carbamate
Autore:
Ortiz, J; Guijarro, A; Yus, M;
Indirizzi:
Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain Univ Alicante Alicante Spain 03080 ept Quim Organ, Alicante 03080, Spain
Titolo Testata:
TETRAHEDRON
fascicolo: 15, volume: 55, anno: 1999,
pagine: 4831 - 4842
SICI:
0040-4020(19990409)55:15<4831:AMBDLO>2.0.ZU;2-N
Fonte:
ISI
Lingua:
ENG
Soggetto:
LITHIOAMINE SYNTHETIC EQUIVALENTS; TIN-LITHIUM EXCHANGE; ENANTIOSELECTIVE SYNTHESES; CONFIGURATIONAL STABILITY; ORGANOLITHIUM COMPOUNDS; ASYMMETRIC-SYNTHESIS; DERIVATIVES; GENERATION; ALCOHOLS; NITROGEN;
Keywords:
lithiation; catalysis; lithium and compounds;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
46
Recensione:
Indirizzi per estratti:
Indirizzo: Yus, M UnivnAlicante, Fac Ciencias, Dept Quim Organ, Apdo 99, Alicante 03080, Spai Univ Alicante Apdo 99 Alicante Spain 03080 9, Alicante 03080, Spai
Citazione:
J. Ortiz et al., "alpha-aminated methyllithium by DTBB-catalysed lithiation of a N-(chloromethyl)carbamate", TETRAHEDRON, 55(15), 1999, pp. 4831-4842

Abstract

The reaction of O-tert-butyl-N-(chloromethyl)-N-methyl carbamate(1) with lithium powder and a catalytic amount of 4,4'-di-tert-butylbiphenyl (DTBB, 2.5 mol %) in the presence of different electrophiles [Me3SiCl, (BuCHO)-Bu-i, (BuCHO)-Bu-t, PhCHO, 4-MeOC6H4CHO, (CH2)(4)CO, (MeCOPr)-Pr-n, Et2CO, MeCO(CH2)(2)CH=CH2, PhCOMe, PhCOnBu, Ph2CO] in THF at -78 degrees C leads, after hydrolysis with water, to the expected functionalised carbamates 2. Carbamates 2 derived from carbonyl compounds are deprotected with hydrogen chloride (for aromatic aldehyde or ketone derivatives) or with a mixture of phenol and trimethylsilyl chloride (for aliphatic aldehyde derivatives) giving substituted 1,2-diols 4. (C) 1999 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 30/03/20 alle ore 19:29:03