Journal of Organic Chemistry, volume 79, issue 21, pages 10648-10654
Selective Formation of a Z-Trisubstituted Double Bond Using a 1-(tert-Butyl)tetrazolyl Sulfone
Adriana Lorente
1, 2
,
Fernando Albericio
1, 2, 3, 4
,
Mercedes Álvarez
1, 2, 5
2
CIBER-BBN,
Networking Center on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, 08028 Barcelona, Spain
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Publication type: Journal Article
Publication date: 2014-10-14
Journal:
Journal of Organic Chemistry
scimago Q2
SJR: 0.724
CiteScore: 6.2
Impact factor: 3.3
ISSN: 00223263, 15206904
PubMed ID:
25280270
Organic Chemistry
Abstract
In 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.
Found
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