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Synfacts 2006(10): 0996-0996  
DOI: 10.1055/s-2006-949347
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of β-Lactams Using Menthone Auxiliary Induction

Contributor(s): Victor Snieckus, Yigang Zhao
Q. Yuan, S.-Z. Jian, Y.-G. Wang*
Zhejiang University, Hangzhou, P. R. of China
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Publikationsdatum:
21. September 2006 (online)

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Significance

Treatment of α-bromoimides 1, readily derived from salicylamide and (-)-menth­one, with imines 2 under Reformatsky conditions leads to trans-β-lactams 3 in good yields and with modest induction. Recrystallization affords optically pure products. The net reaction leads to the regeneration of the chiral auxiliary 4 which can be recycled. The scope of the reaction was insufficiently explored.