Literature DB >> 26833255

An Asymmetric Vinylogous Michael Cascade of Silyl Glyoximide, Vinyl Grignard, and Nitroalkenes via Long Range Stereoinduction.

Gregory R Boyce1, Jeffrey S Johnson2.   

Abstract

A diastereoselective auxiliary-mediated vinylation/[1,2]-Brook rearrangement/vinylogous Michael cascade of silyl glyoximide, vinylmagnesium bromide, and nitroalkenes is described. The reaction occurs with complete regio- and diastereocontrol in good yield. The diastereoselectivity is induced by a rare instance of 1,7-chirality transfer that is hypothesized to arise from a trans-multihetero-decalin transition state.

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Year:  2016        PMID： 26833255      PMCID： PMC4761320          DOI： 10.1021/acs.joc.5b02693

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  25 in total

1.  Dienamine-mediated inverse-electron-demand hetero-diels-alder reaction by using an enantioselective H-bond-directing strategy.

Authors:  Lukasz Albrecht; Gustav Dickmeiss; Christian F Weise; Carles Rodríguez-Escrich; Karl Anker Jørgensen
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-12       Impact factor: 15.336

2.  Catalytic, enantioselective vinylogous Michael reactions.

Authors:  Christoph Schneider; Falko Abels
Journal:  Org Biomol Chem       Date:  2014-04-23       Impact factor: 3.876

3.  Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.

Authors:  Gregory R Boyce; Stephen N Greszler; Jeffrey S Johnson; Xin Linghu; Justin T Malinowski; David A Nicewicz; Andrew D Satterfield; Daniel C Schmitt; Kimberly M Steward
Journal:  J Org Chem       Date:  2012-03-23       Impact factor: 4.354

4.  Three-component coupling reactions of silylglyoxylates, alkynes, and aldehydes: a chemoselective one-step glycolate aldol construction.

Authors:  David A Nicewicz; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2005-05-04       Impact factor: 15.419

Review 5.  Catalytic, enantioselective, vinylogous aldol reactions.

Authors:  Scott E Denmark; John R Heemstra; Gregory L Beutner
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-25       Impact factor: 15.336

6.  Rationally designed multifunctional supramolecular iminium catalysis: direct vinylogous Michael addition of unmodified linear dienol substrates.

Authors:  Yun Gu; Yao Wang; Tian-Yang Yu; Yong-Min Liang; Peng-Fei Xu
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-19       Impact factor: 15.336

7.  Three-component reactions of sulfonylimidates, silyl glyoxylates and N-tert-butanesulfinyl aldimines: an efficient, diastereoselective, and enantioselective synthesis of Cyclic N-sulfonylamidines.

Authors:  Ming Yao; Chong-Dao Lu
Journal:  Org Lett       Date:  2011-04-26       Impact factor: 6.005

8.  Copper-catalyzed aerobic oxidative amidation of terminal alkynes: efficient synthesis of ynamides.

Authors:  Tetsuya Hamada; Xuan Ye; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2008-01-01       Impact factor: 15.419

9.  Organocatalytic enantioselective vinylogous Michael reaction of vinylketene silyl-N,O-acetals.

Authors:  Smita Basu; Vaishali Gupta; Johannes Nickel; Christoph Schneider
Journal:  Org Lett       Date:  2013-12-16       Impact factor: 6.005

Review 10.  The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis.

Authors:  Markus Kalesse; Martin Cordes; Gerrit Symkenberg; Hai-Hua Lu
Journal:  Nat Prod Rep       Date:  2014-03-05       Impact factor: 13.423
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