Highly general synthesis of [E]- and [Z]-3-alkylsubstituted allylboronates via one-carbon homologation of stereospecific 1-alken-1-ylboronates
1993; Elsevier BV; Volume: 34; Issue: 49 Linguagem: Inglês
10.1016/s0040-4039(00)61491-0
ISSN1873-3581
AutoresHerbert C. Brown, Avinash Phadke, Narayan G. Bhat,
Tópico(s)Advanced Synthetic Organic Chemistry
ResumoStereospecific 1-alken-1-ylboronates readily react with in situ generated chloromethyllithium, producing the corresponding allylboronate in good yields and in excellent stereochemical purities. These are very important synthetic intermediates and conversion of a representative derivative, [E]-2-(2-heptenyl)-1,3,2-dioxaborinane, 2 (R1 = C4H9, R2 = R3 = H), into several compounds of synthetic interest is described.
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