Unique selectivity of iodohydroxylation reaction of allenyl phenyl sulfoxides in aqueous MeCN. A stereodefined synthesis of (E)-2-iodo-3-hydroxy-1-alkenyl sulfoxides

S Ma; Q Wei; H Wang

doi:10.1021/ol006639p

Unique selectivity of iodohydroxylation reaction of allenyl phenyl sulfoxides in aqueous MeCN. A stereodefined synthesis of (E)-2-iodo-3-hydroxy-1-alkenyl sulfoxides

Org Lett. 2000 Nov 30;2(24):3893-5. doi: 10.1021/ol006639p.

Authors

S Ma¹, Q Wei, H Wang

Affiliation

¹ Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China.

PMID: 11101447
DOI: 10.1021/ol006639p

Abstract

Iodohydroxylation reaction of allenyl phenyl sulfoxides with I(2) can smoothly proceed to generate (E)-2-iodo-3-hydroxy-1-alkenyl sulfoxides with excellent regio- and stereoselectivity in high or excellent yields. The configuration of E-2a was determined by the X-ray diffraction study.