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Complementary Strategy for Regioselective Synthesis of Diverse β‐Hydroxysulfones from Thiosulfonates
Author(s) -
Son Soobin,
Shyam Pranab K.,
Park Hyowon,
Jeong Ilgyo,
Jang HyeYoung
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800778
Subject(s) - chemistry , regioselectivity , nucleophile , nucleophilic addition , combinatorial chemistry , organic chemistry , catalysis
The regioselective synthesis of variously substituted β‐hydroxysulfones from thiosulfonates was developed. The reactions of thiosulfonates and alkenes via a peroxy radical intermediate provided 2° and 3° β‐hydroxysulfones in good yields. The presence of epoxides instead of alkenes changed the reaction mechanism to nucleophilic addition involving sulfinate anions to afford 1° and 2° β‐hydroxysulfones. By using both protocols, the regiochemical outcome of the β‐hydroxysulfones synthesized from thiosulfonates was diversified.