Literature DB >> 21553930

Diastereoselectively switchable enantioselective trapping of carbamate ammonium ylides with imines.

Jun Jiang1, Hua-Dong Xu, Jian-Bei Xi, Bai-Yan Ren, Feng-Ping Lv, Xin Guo, Li-Qin Jiang, Zhi-Yong Zhang, Wen-Hao Hu.   

Abstract

The diastereoselectively switchable enantioselective trapping of protic carbamate ammonium ylides with imines is reported. The intriguing Rh(2)(OAc)(4) and chiral Brønsted acid cocatalyzed three-component Mannich-type reaction of a diazo compound, a carbamate, and an imine provides rapid and efficient access to both syn- and anti-α-substituted α,β-diamino acid derivatives with a high level control of chemo-, diastereo-, and enantioselectivity.

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Year:  2011        PMID: 21553930     DOI: 10.1021/ja201589k

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  12 in total

1.  Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids.

Authors:  Andrew J Neel; Jörg P Hehn; Pascal F Tripet; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

2.  Cinchonidinium acetate as a convenient catalyst for the asymmetric synthesis of cis-stilbenediamines.

Authors:  Ryan R Walvoord; Marisa C Kozlowski
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3.  Highly enantioselective trapping of zwitterionic intermediates by imines.

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Journal:  Nat Chem       Date:  2012-07-29       Impact factor: 24.427

4.  Functionalized Spiroindolines with Anticancer Activity through a Metal-Free Post-Ugi Diastereoselective One-Pot Cascade Reaction.

Authors:  Zhi-Gang Xu; Shi-Qiang Li; Jiang-Ping Meng; Dian-Yong Tang; Liu-Jun He; Jie Lei; Hui-Kuan Lin; Hong-Yu Li; Zhong-Zhu Chen
Journal:  Chemistry       Date:  2018-04-20       Impact factor: 5.236

5.  Cyclopropenimine-catalyzed enantioselective Mannich reactions of tert-butyl glycinates with N-Boc-imines.

Authors:  Jeffrey S Bandar; Tristan H Lambert
Journal:  J Am Chem Soc       Date:  2013-08-01       Impact factor: 15.419

6.  Synergistic Catalysis: A Powerful Synthetic Strategy for New Reaction Development.

Authors:  Anna E Allen; David W C Macmillan
Journal:  Chem Sci       Date:  2012-01-25       Impact factor: 9.825

7.  The combined C-H functionalization/Cope rearrangement: discovery and applications in organic synthesis.

Authors:  Huw M L Davies; Yajing Lian
Journal:  Acc Chem Res       Date:  2012-05-11       Impact factor: 22.384

8.  A Diastereodivergent and Enantioselective Approach to syn- and anti-Diamines: Development of 2-Azatrienes for Cu-Catalyzed Reductive Couplings with Imines That Furnish Allylic Amines.

Authors:  Pengfei Zhou; Xinxin Shao; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2021-08-23       Impact factor: 16.383

9.  Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe.

Authors:  Motoyuki Isoda; Kazuyuki Sato; Yurika Kunugi; Satsuki Tokonishi; Atsushi Tarui; Masaaki Omote; Hideki Minami; Akira Ando
Journal:  Beilstein J Org Chem       Date:  2016-07-27       Impact factor: 2.883

10.  A Rh(II)-catalyzed multicomponent reaction by trapping an α-amino enol intermediate in a traditional two-component reaction pathway.

Authors:  Shunying Liu; Wenfeng Yao; Yuan Liu; Qinghua Wei; Jianghui Chen; Xiang Wu; Fei Xia; Wenhao Hu
Journal:  Sci Adv       Date:  2017-03-08       Impact factor: 14.136

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