Organocatalyzed Annulation Cascade toward Asymmetric Functionalization of Dibenzoxazepines and Dibenzothiazepines with Vicinal Tertiary Stereogenic Centers | Zendy

Ramakrishna Isai | Zendy; Reddy Mallu Kesava | Zendy; Baidya Mahiuddin | Zendy

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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.

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