Literature DB >> 18630924

A highly diastereo- and enantioselective synthesis of multisubstituted cyclopentanes with four chiral carbons by the organocatalytic domino Michael-Henry reaction.

Bin Tan1, Pei Juan Chua, Xiaofei Zeng, Min Lu, Guofu Zhong.   

Abstract

Highly functionalized cyclopentanes with four stereogenic carbons including two quaternary stereocenters have been synthesized in excellent yields (90-95%) with complete diastereoselectivities and excellent enantioselectivities (88-96% ee) by the organocatalyzed asymmetric domino Michael-Henry reaction.

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Year:  2008        PMID: 18630924     DOI: 10.1021/ol801273x

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


  9 in total

1.  Enantioselective synthesis of bicylco[3.2.1]octan-8-ones using a tandem Michael-Henry reaction.

Authors:  Derong Ding; Cong-Gui Zhao; Qunsheng Guo; Hadi Arman
Journal:  Tetrahedron       Date:  2010-06-19       Impact factor: 2.457

2.  Three-component coupling reactions of silyl glyoxylates, vinyl Grignard reagent, and nitroalkenes: an efficient, highly diastereoselective approach to nitrocyclopentanols.

Authors:  Gregory R Boyce; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-15       Impact factor: 15.336

3.  Organocatalyzed synthesis of 2-amino-8-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles.

Authors:  Derong Ding; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2010-03-03       Impact factor: 2.415

4.  Organocatalyzed enantioselective synthesis of 6-amino-5-cyanodihydropyrano[2,3-c]pyrazoles.

Authors:  Sanjib Gogoi; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2009-05-13       Impact factor: 2.415

5.  Asymmetric synthesis of fully substituted cyclopentane-oxindoles through an organocatalytic triple Michael domino reaction.

Authors:  Liang-Hua Zou; Arne R Philipps; Gerhard Raabe; Dieter Enders
Journal:  Chemistry       Date:  2014-12-02       Impact factor: 5.236

6.  Synergistic chiral iminium and palladium catalysis: Highly regio- and enantioselective [3 + 2] annulation reaction of 2-vinylcyclopropanes with enals.

Authors:  Haipan Zhu; Peile Du; Jianjun Li; Ziyang Liao; Guohua Liu; Hao Li; Wei Wang
Journal:  Beilstein J Org Chem       Date:  2016-06-29       Impact factor: 2.883

7.  Polyhydroxylated Cyclopentane β-Amino Acids Derived from d-Mannose and d-Galactose: Synthesis and Protocol for Incorporation into Peptides.

Authors:  Fernando Fernández; Alberto G Fernández; Rosalino Balo; Víctor M Sánchez-Pedregal; Miriam Royo; Raquel G Soengas; Ramón J Estévez; Juan C Estévez
Journal:  ACS Omega       Date:  2022-01-04

8.  Asymmetric domino synthesis of indanes bearing four contiguous stereocentres catalyzed by sub-mol% loadings of a squaramide in minutes.

Authors:  Charles C J Loh; Daniel Hack; Dieter Enders
Journal:  Chem Commun (Camb)       Date:  2013-11-11       Impact factor: 6.222

9.  Pot and time economies in the total synthesis of Corey lactone.

Authors:  Nariyoshi Umekubo; Yurina Suga; Yujiro Hayashi
Journal:  Chem Sci       Date:  2019-12-23       Impact factor: 9.825

  9 in total

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