jo501988e_si_001.pdf (3.66 MB)
Selective Formation of a Z‑Trisubstituted Double Bond Using a 1‑(tert-Butyl)tetrazolyl Sulfone
journal contribution
posted on 2014-11-07, 00:00 authored by Adriana Lorente, Fernando Albericio, Mercedes ÁlvarezIn
our effort to gain further insight into the enantioselective
synthesis of the structural core of phormidolides B and C, we have
discovered the formation of a Z-trisubstituted double
bond. Here, we describe a highly selective process that can be applied
to our target following a strategy that is based on Julia–Kocienski
olefination. The use of 1-(tert-butyl)tetrazolyl
sulfone affords the construction of the Z-trisubstituted
alkene with high efficiency and stereoselectivity.