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Intramolecular, Reductive Cyclization of β‐Ketoisothiocyanates Promoted by Using Samarium Diiodide
Author(s) -
Cho Min Seok,
Lee In Sang,
Kang Sung Ho,
Kim Yong Hae
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400676
Subject(s) - samarium diiodide , intramolecular force , samarium , chemistry , ammonium thiocyanate , stereoselectivity , beta (programming language) , medicinal chemistry , alpha (finance) , intramolecular reaction , stereochemistry , organic chemistry , catalysis , medicine , construct validity , nursing , computer science , patient satisfaction , programming language
A novel samarium diiodide (SmI 2 ) promoted intramolecular cyclization of β‐ketoisothiocyanate, derived from α,β‐unsaturated esters and ammonium thiocyanate led to α‐hydroxythiolactams and/or thiolactams in high yields. Treatment of β‐ketoisothiocyanate with two equivalents of SmI 2 gave a mixture of α‐hydroxythiolactam and thiolactam. Four equivalents of SmI 2 afforded only thiolactam in high yields. The intramolecular cyclization took place with high to complete stereoselectivity. A mechanism to explain this transformation is proposed.