F. D'aniello, A. Mann, Duccio Mattii
Jul 1, 1994
Citations
0
Influential Citations
20
Citations
Journal
Journal of Organic Chemistry
Abstract
2-Substituted 3-(trimethylsilyl)-1-propenes react with N-Boc-α-amino aldehydes in the presence of BF 3 -OEt 2 to give homoallylic alcohols, potential intermediates for the synthesis of hydroxyethylene peptide isosteres. The reaction gives a predominance of the syn products, but 2-(chloromethyl)3-(trimethylsilyl)-1-propene (5) exhibits a higher ste- reoselectivity with respect to other analogous allylsilanes. We hypot- hesize that thus selectivity is due to an «ene» reaction followed by desilylation in the reaction medium (BF 3 -OEt 2 , CHCl 3 ). This reaction shows applicability to the synthesis of potential HIV-1 protease inhi- bitors. The preparation of compound (3), which has a structure related to the potent inhibitor L-682,679, is described