Issue 6, 2017

Organobase-catalyzed [1,2]-Brook rearrangement of silyl glyoxylates

Abstract

A highly efficient [1,2]-Brook rearrangement of silyl glyoxylates has been developed using DBU as the organobase-catalyst. This [1,2]-Brook rearrangement is applicable to a number of thiols and secondary phosphine oxides containing acidic protons. These nucleophiles afford the corresponding Brook products in high yields. Using this methodology, a formal synthesis of anti-HIV drug compound lamivudine was realized.

Graphical abstract: Organobase-catalyzed [1,2]-Brook rearrangement of silyl glyoxylates

Supplementary files

Article information

Article type
Paper
Submitted
01 Jan 2017
Accepted
11 Jan 2017
First published
11 Jan 2017

Org. Biomol. Chem., 2017,15, 1418-1425

Organobase-catalyzed [1,2]-Brook rearrangement of silyl glyoxylates

M. Han, F. Yang, D. Zhou and Z. Xu, Org. Biomol. Chem., 2017, 15, 1418 DOI: 10.1039/C7OB00005G

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