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Modified Asymmetric Strecker Reaction of Aldehyde with Secondary Amine: A Protocol for the Synthesis of S-Clopidogrel (An Antiplatelet Agent)

Author:
Sadhukhan, Arghya, Saravanan, S., Khan, Noor-ul H., Kureshy, Rukhsana I., Abdi, Sayed H. R., Bajaj, Hari C.
Source:
Journal of organic chemistry 2012 v.77 no.16 pp. 7076-7080
ISSN:
1520-6904
Subject:
aldehydes, catalysts, organic chemistry, sodium fluoride
Abstract:
A first approach for catalytic asymmetric Strecker reaction of aldehydes with a secondary amine in the presence of sodium fluoride using hydroquinine as chiral catalyst was developed. The catalytic system gave α-aminonitriles in excellent yields (up to 95%) and high enantioselectivities (er up to 94:6). The efficacy of the chiral product was successfully fulfilled in the improved synthesis of (S)-clopidogrel (an antiplatelet agent).
Agid:
5498963