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Synlett 1998; 1998(3): 275-276
DOI: 10.1055/s-1998-1624
DOI: 10.1055/s-1998-1624
letter
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Enantioselective Synthesis of α-Methylene-γ-Lactams. Nucleophilic Addition of a Chirally Modified β-Functionalized Allylboronate Reagent to Imines
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
![](https://www.thieme-connect.de/media/synlett/199803/lookinside/thumbnails/10.1055-s-1998-1624-1.jpg)
The reaction of β-functionalized allylboronate 1 derived from endo-2-phenyl-exo-2,3-bornanediol with imines affords homoallylic amines and α-methylene-γ-lactams in good yields and high enantioselectivity (ee ≥94%). A mechanism of the carbalkoxyallylboration reaction is proposed to explain the excellent asymmetric induction.
chiral β-functionalized allylboronate - endo-2-phenyl-exo-2,3-bornanediol - α-trimethylsilyl-imines - α-methylene-γ-lactams - homoallylic amines