Highly stereoselective chlorination of beta-substituted cyclic alcohols using PPh3-NCS: factors that control the stereoselectivity.
A variety of trans-beta-substituted cyclic alcohols were stereoselectively chlorinated to either the corresponding cis-chloride or trans-chloride (inversion or retention of configuration) with good to excellent yields; the stereochemical outcome is determined by the size of the ring and the nature of the beta-substituents, especially the electronegativity of the substituted atom.
Jaseer
E A
EA
Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu, 600 036, India.
Naidu
Ajay B
AB
Kumar
Sreehari S
SS
Rao
R Koteshwar
RK
Thakur
Krishna G
KG
Sekar
G
G