Highly diastereoselective strecker reaction of enolizable aliphatic sulfinimines.
The reaction of chiral sulfinimines 1c-g derived from aliphatic aldehydes with TMSCN in the presence of CsF gave alpha-amino nitriles in high diastereoselectivity and yield. alpha,beta-Diamino acid derivatives were also obtained in high diastereoselectivity from the reaction of 2-aziridinesulfinimines 1h and 1i followed by ring-opening of the products with thiophenol. The presence of hydrogen at the alpha-position of the C=N double bond is crucial in this TMSCN addition reaction.
Li
Bin-Feng
BF
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Yuan
Ke
K
Zhang
Ming-Jie
MJ
Wu
Hao
H
Dai
Li-Xin
LX
Wang
Quan Rui
QR
Hou
Xue-Long
XL