Literature DB >> 25699577

Enantioselective bromocyclization of allylic amides catalyzed by BINAP derivatives.

Yuji Kawato1, Akino Kubota, Hiromi Ono, Hiromichi Egami, Yoshitaka Hamashima.   

Abstract

A highly enantioselective bromocyclization of allylic amides with N-bromosuccinimide (NBS) was developed with DTBM-BINAP as a catalyst, affording chiral oxazolines with a tetrasubstituted carbon center in high yield with up to 99% ee. By utilizing the bromo substituent as a handle, the obtained compounds were converted to synthetically useful chiral building blocks.

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Year:  2015        PMID: 25699577     DOI: 10.1021/acs.orglett.5b00220

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  Enantioselective Synthesis of γ-Lactams by Lewis Base Catalyzed Sulfenoamidation of Alkenes.

Authors:  Jesse L Panger; Scott E Denmark
Journal:  Org Lett       Date:  2019-12-20       Impact factor: 6.005

2.  A catalytic highly enantioselective allene approach to oxazolines.

Authors:  Hongwen Luo; Zheng Yang; Weilong Lin; Yangguangyan Zheng; Shengming Ma
Journal:  Chem Sci       Date:  2018-01-05       Impact factor: 9.825

3.  Umpolung carbonyls enable direct allylation and olefination of carbohydrates.

Authors:  Jian Kan; Zhangpei Chen; Zihang Qiu; Leiyang Lv; Chenchen Li; Chao-Jun Li
Journal:  Sci Adv       Date:  2022-03-09       Impact factor: 14.136

4.  Ritter-enabled catalytic asymmetric chloroamidation of olefins.

Authors:  Daniel C Steigerwald; Bardia Soltanzadeh; Aritra Sarkar; Cecilia C Morgenstern; Richard J Staples; Babak Borhan
Journal:  Chem Sci       Date:  2020-12-07       Impact factor: 9.825

  4 in total

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