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Organocatalyzed Annulation Cascade toward Asymmetric Functionalization of Dibenzoxazepines and Dibenzothiazepines with Vicinal Tertiary Stereogenic Centers
Author(s) -
Ramakrishna Isai,
Reddy Mallu Kesava,
Baidya Mahiuddin
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201902496
Subject(s) - stereocenter , annulation , vicinal , stereoselectivity , cascade reaction , chemistry , organocatalysis , surface modification , enantioselective synthesis , combinatorial chemistry , derivatization , stereochemistry , catalysis , organic chemistry , high performance liquid chromatography
An efficient organocatalyzed annulation cascade has been established for the stereoselective functionalization of dibenzoxazepine and dibenzothiazepine scaffolds. The protocol used ready‐stock proline as a catalyst and a variety biologically important oxa/thiazepine based polycyclic frameworks featuring congested chiral vicinal tertiary centers were obtained in high yields and excellent diastereoselectivities (>20:1 dr) and enantioselectivities (>96:4 er). Synthetic utility was showcased through the gram‐scale reaction and diverse derivatization sequences.