Effective tuning of the arene and alkanesulfinamides for highly enantioselective synthesis of (S)-4-chlorophenylphenylmethylamine, a key intermediate for antihistamic (S)-cetirizine
2003; Elsevier BV; Volume: 44; Issue: 22 Linguagem: Inglês
10.1016/s0040-4039(03)00903-1
ISSN1873-3581
AutoresZhengxu S. Han, Dhileepkumar Krishnamurthy, Paul Grover, Q. Kevin Fang, Derek A. Pflum, Chris H. Senanayake,
Tópico(s)Chemical Synthesis and Analysis
ResumoHigh diastereoselectivity (>94%) has been achieved in the phenylMgBr addition process to chlorophenyl aldimine derived from the new and sterically hindered triisopropylbenzene sulfinamide (TIPBSA) in the synthesis of a key intermediate of (S)-Cetirizine. Surprisingly, under the same reaction conditions, toluenesulfinamide derived chlorophenyl aldimine provided only 10% ee.
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