Literature DB >> 22545004

Alkenenitrile Transmissive Olefination: Synthesis of the Putative Lignan "Morinol I"

Fraser F Fleming1, Wang Liu, Lihua Yao, Bhaskar Pitta, Matthew Purzycki, P C Ravikumar.   

Abstract

Grignard reagents trigger an addition-elimination with α'-hydroxy acrylonitriles to selectively generate Z-alkenenitriles. The modular assembly of Z-alkenenitriles from a Grignard reagent, acrylonitrile, and an aldehyde is ideal for stereoselectively synthesizing alkenes as illustrated in the synthesis of the putative lignan "morinol I."

Entities:  

Year:  2011        PMID： 22545004      PMCID： PMC3336159          DOI： 10.1002/ejoc.201101235

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  14 in total

1.  Recent advances in the Baylis-Hillman reaction and applications.

Authors:  Deevi Basavaiah; Anumolu Jaganmohan Rao; Tummanapalli Satyanarayana
Journal:  Chem Rev       Date:  2003-03       Impact factor: 60.622

2.  Enantioselective total synthesis of borrelidin.

Authors:  Matthew O Duffey; Arnaud LeTiran; James P Morken
Journal:  J Am Chem Soc       Date:  2003-02-12       Impact factor: 15.419

Review 3.  Recent contributions from the Baylis-Hillman reaction to organic chemistry.

Authors:  Deevi Basavaiah; Bhavanam Sekhara Reddy; Satpal Singh Badsara
Journal:  Chem Rev       Date:  2010-09-08       Impact factor: 60.622

4.  The Baylis-Hillman reaction: a novel source of attraction, opportunities, and challenges in synthetic chemistry.

Authors:  Deevi Basavaiah; Kalapala Venkateswara Rao; Raju Jannapu Reddy
Journal:  Chem Soc Rev       Date:  2007-03-23       Impact factor: 54.564

5.  Phenylpropanol derivatives from morina chinensis

Authors: 
Journal:  J Nat Prod       Date:  1999-10       Impact factor: 4.050

6.  Application of conformation design in acyclic stereoselection: total synthesis of borrelidin as the crystalline benzene solvate.

Authors:  Stephen Hanessian; Yang Yang; Simon Giroux; Vincent Mascitti; Jianguo Ma; Franck Raeppel
Journal:  J Am Chem Soc       Date:  2003-11-12       Impact factor: 15.419

7.  Conversion of allylic alcohols to stereodefined trisubstituted alkenes: a complementary process to the Claisen rearrangement.

Authors:  Justin K Belardi; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2008-12-17       Impact factor: 15.419

8.  Organic reactions in water: an efficient zinc-mediated stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes using unactivated alkyl halides.

Authors:  Biswanath Das; Joydeep Banerjee; Gurram Mahender; Anjoy Majhi
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

9.  Titanocene(III) chloride mediated radical-induced addition to Baylis-Hillman adducts: synthesis of (E)- and (Z)-trisubstituted alkenes and alpha-methylene/arylidene delta-lactones.

Authors:  Samir K Mandal; Moumita Paira; Subhas C Roy
Journal:  J Org Chem       Date:  2008-04-22       Impact factor: 4.354

10.  Total synthesis of (-)-borrelidin.

Authors:  Tohru Nagamitsu; Daisuke Takano; Takeo Fukuda; Kazuhiko Otoguro; Isao Kuwajima; Yoshihiro Harigaya; Satoshi Omura
Journal:  Org Lett       Date:  2004-05-27       Impact factor: 6.005
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  1 in total

1.  Transmissive olefination route to putative "morinol I" lignans.

Authors:  Lihua Yao; Bhaskar Pitta; P C Ravikumar; Matthew Purzycki; Fraser F Fleming
Journal:  J Org Chem       Date:  2012-03-20       Impact factor: 4.354
  1 in total

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