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Titolo:
Simple procedures for the preparation of (Z)-2-(1-trimethylsilyl-1-alkenyl)-1,3,2-dioxaborinanes
Autore:
Bhat, NG; Aguirre, CP;
Indirizzi:
Univ Texas Pan Amer, Dept Chem, Edinburg, TX 78539 USA Univ Texas Pan Amer Edinburg TX USA 78539 pt Chem, Edinburg, TX 78539 USA
Titolo Testata:
TETRAHEDRON LETTERS
fascicolo: 42, volume: 41, anno: 2000,
pagine: 8027 - 8031
SICI:
0040-4039(20001014)41:42<8027:SPFTPO>2.0.ZU;2-L
Fonte:
ISI
Lingua:
ENG
Soggetto:
HIGH ENANTIOMERIC PURITIES; ASYMMETRIC HYDROBORATION; ESTERS; DIISOPINOCAMPHEYLBORANE; SILYLACETYLENES; ORGANOBORANES; OXIDATION; ALKENES; ACIDS;
Keywords:
gem-dimetallic; stereospecific; diisopinocampheylborane; acetaldehyde; dichloroborane;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
19
Recensione:
Indirizzi per estratti:
Indirizzo: Bhat, NG Univ Texas Pan Amer, Dept Chem, 1201 W Univ Dr, Edinburg, TX 78539 USA Univ Texas Pan Amer 1201 W Univ Dr Edinburg TX USA 78539 8539 USA
Citazione:
N.G. Bhat e C.P. Aguirre, "Simple procedures for the preparation of (Z)-2-(1-trimethylsilyl-1-alkenyl)-1,3,2-dioxaborinanes", TETRAHEDR L, 41(42), 2000, pp. 8027-8031

Abstract

Two simple procedures for obtaining (Z)-2-(1-trimethylsilyl-1-alkenyl)-1,3,2-dioxaborinanes based on 1-trimethylsilyl-1-alkynes are described. In thefirst procedure, 1-trimethylsilyl-1-alkynes are hydroborated with diisopinocampheylborane to provide the corresponding (Z)-2-(trimethylsily1-1-alkenyl)-diisopinocampheylboranes. These are then reacted with excess acetaldehyde to afford the corresponding (2)-2-(1-trimethylsilyl-1-alkenyl)-diethoxyboranes which are esterified with 1,3-propane diol to give the (2)-2-(1-trimethylsilyl-1-alkenyl)-1,3,2-dioxaborinanes in good yields and in high stereochemical purities. In the second procedure, 1-trimethylsilyl-1-alkynes are hydroborated with dichloroborane-methyl sulfide complex in the presence of a stoichiometric amount of boron trichloride in hexane, followed by treatment with 1,3-propane diol. These novel stereodefined gem-alkenyldimetaliic compounds containing boron and silicon are isolated and characterized by NMR(H-1 and C-13) spectral data. (C) 2000 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 28/09/20 alle ore 11:23:52