Long-range diastereoselectivity in Ugi reactions of 2-substituted dihydrobenzoxazepines

Beilstein Journal of Organic Chemistry

Andrea Basso¹  Valeria Rocca¹  Luca Banfi¹  Renata Riva¹  Valentina Cerulli¹ 

[1] Department of Chemistry and Industrial Chemistry, University of Genova, I-16146 Genova, Italy;

关键词: benzoxazepines;    cyclic imines;    long range stereoinduction;    multicomponent reactions;    Ugi reaction;   

DOI  :  10.3762/bjoc.7.109

来源: DOAJ

【 摘 要 】

The Ugi reaction of 2-substituted dihydrobenzoxazepines was found to proceed with unexpectedly good diastereoselectivitiy (diastereoisomeric ratios up to 9:1), despite the large distance between the pre-existing stereogenic centre and the newly generated one. This result represents the first good 1,4 asymmetric induction in an Ugi reaction as well as the first example of diastereoselective Ugi reaction of seven membered cyclic imines. It allows the diversity-oriented synthesis of various tetrahydro[f][1,4]benzoxazepines.

【 授权许可】

Unknown