Literature DB >> 23926881

Organocatalyzed formal [2 + 2] cycloaddition of ketimines with allenoates: facile access to azetidines with a chiral tetrasubstituted carbon stereogenic center.

Shinobu Takizawa1, Fernando Arteaga Arteaga, Yasushi Yoshida, Michitaka Suzuki, Hiroaki Sasai.   

Abstract

An enantioselective organocatalyzed aza-MBH-type reaction of ketimines and allenoates has been developed. The present formal [2 + 2] cycloaddition produces highly functionalized azetidines with a chiral tetrasubstituted carbon stereogenic center in good to excellent yields and high enantioselectivities.

Entities:  

Year:  2013        PMID： 23926881     DOI： 10.1021/ol401817q

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


  4 in total

1.  A Stereoselective [3+1] Ring Expansion for the Synthesis of Highly Substituted Methylene Azetidines.

Authors:  Steven C Schmid; Ilia A Guzei; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-01       Impact factor: 15.336

2.  Oxidative allene amination for the synthesis of nitrogen-containing heterocycles.

Authors:  Josephine Eshon; Nels C Gerstner; Jennifer M Schomaker
Journal:  ARKIVOC       Date:  2018-11-26       Impact factor: 1.140

3.  Determination of the absolute configuration of compounds bearing chiral quaternary carbon centers using the crystalline sponge method.

Authors:  Shiho Sairenji; Takashi Kikuchi; Mohamed Ahmed Abozeid; Shinobu Takizawa; Hiroaki Sasai; Yuichiro Ando; Kohsuke Ohmatsu; Takashi Ooi; Makoto Fujita
Journal:  Chem Sci       Date:  2017-05-16       Impact factor: 9.825

4.  Organocatalytic Access to Enantioenriched Spirooxindole-Based 4-Methyleneazetidines.

Authors:  Giulia Rainoldi; Matteo Faltracco; Claudia Spatti; Alessandra Silvani; Giordano Lesma
Journal:  Molecules       Date:  2017-11-21       Impact factor: 4.411
  4 in total

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