Literature DB >> 16119914

Dual catalyst control in the enantioselective intramolecular Morita-Baylis-Hillman reaction.

Carrie E Aroyan1, Melissa M Vasbinder, Scott J Miller.   

Abstract

The intramolecular Morita-Baylis-Hillman (MBH) reaction has been achieved with unprecedented levels of enantioselectivity. Using a co-catalyst system involving pipecolinic acid and N-methylimidazole, cyclic MBH products have been obtained with enantiomer ratios of 92:8 (84% ee). In addition, reactions may be carried out with a "kinetic resolution quench" involving acetic anhydride and an asymmetric acylation catalyst such that ee enhancement occurs to deliver products with >98% ee with an isolated yield of 50%. [reaction: see text]

Entities:  

Year:  2005        PMID： 16119914     DOI： 10.1021/ol0513544

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


  6 in total

1.  Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids.

Authors:  Yonggui Chi; Li Guo; Nathan A Kopf; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2008-04-04       Impact factor: 15.419

2.  Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using L-pipecolinic acid and substituted guanidine organocatalysts.

Authors:  Bhaskar C Das; Seetaram Mohapatra; Philip D Campbell; Sabita Nayak; Sakkarapalayam M Mahalingam; Todd Evans
Journal:  Tetrahedron Lett       Date:  2010-05-01       Impact factor: 2.415

3.  Pipecolic acid-catalyzed direct asymmetric mannich reactions.

Authors:  Paul Ha-Yeon Cheong; Haile Zhang; Rajee Thayumanavan; Fujie Tanaka; K N Houk; Carlos F Barbas
Journal:  Org Lett       Date:  2006-03-02       Impact factor: 6.005

4.  Synthesis of sultam scaffolds via intramolecular oxa-Michael and diastereoselective Baylis-Hillman reactions.

Authors:  Aihua Zhou; Paul R Hanson
Journal:  Org Lett       Date:  2008-06-14       Impact factor: 6.005

Review 5.  Enantioselective, organocatalytic Morita-Baylis-Hillman and Aza-Morita-Baylis-Hillman reactions: stereochemical issues.

Authors:  Javier Mansilla; José M Saá
Journal:  Molecules       Date:  2010-02-01       Impact factor: 4.411

6.  Mini-ISES identifies promising carbafructopyranose-based salens for asymmetric catalysis: Tuning ligand shape via the anomeric effect.

Authors:  Kannan R Karukurichi; Xiang Fei; Robert A Swyka; Sylvain Broussy; Weijun Shen; Sangeeta Dey; Sandip K Roy; David B Berkowitz
Journal:  Sci Adv       Date:  2015-07-10       Impact factor: 14.136
  6 in total

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