Literature DB >> 27487461

Mechanistically Inspired Route toward Hexahydro-2H-chromenes via Consecutive [4 + 2] Cycloadditions.

Kumar Dilip Ashtekar1, Xinliang Ding1, Edmond Toma1, Wei Sheng1, Hadi Gholami1, Christopher Rahn1, Paul Reed1, Babak Borhan1.   

Abstract

Utilizing two robust C-C bond-forming reactions, the Baylis-Hillman reaction and the Diels-Alder reaction, we report a highly enantio-, regio-, and diastereoselective synthesis of hexahydro-2H-chromenes via two sequential [4 + 2] cycloadditions. These tandem and formal cycloadditions have also been performed as a "one-pot" sequence to access the corresponding heterocycles constituting up to five contiguous stereocenters in excellent yields and stereoselectivity.

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Year:  2016        PMID： 27487461      PMCID： PMC5342895          DOI： 10.1021/acs.orglett.6b01742

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


  11 in total

Review 1.  The Diels--Alder reaction in total synthesis.

Authors:  K C Nicolaou; Scott A Snyder; Tamsyn Montagnon; Georgios Vassilikogiannakis
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

Review 2.  Catalytic enantioselective Diels--Alder reactions: methods, mechanistic fundamentals, pathways, and applications.

Authors:  E J Corey
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

3.  Origins of the diastereoselectivity in hydrogen bonding directed Diels-Alder reactions of chiral dienes with achiral dienophiles: a computational study.

Authors:  Sesil Agopcan; Nihan Çelebi-Ölçüm; Melek Nihan Üçışık; Amitav Sanyal; Viktorya Aviyente
Journal:  Org Biomol Chem       Date:  2011-10-11       Impact factor: 3.876

4.  Highly enantioselective synthesis of 3,4-dihydropyrans through a phosphine-catalyzed [4+2] annulation of allenones and β,γ-unsaturated α-keto esters.

Authors:  Weijun Yao; Xiaowei Dou; Yixin Lu
Journal:  J Am Chem Soc       Date:  2014-12-08       Impact factor: 15.419

5.  Enantioselective Amine-Catalyzed [4 + 2] Annulations of Allene Ketones and 2,3-Dioxopyrrolidine Derivatives: Synthesis of 4H-Pyran Derivatives.

Authors:  Shuang Zhang; Yong-Chun Luo; Xiu-Qin Hu; Zhu-Yin Wang; Yong-Min Liang; Peng-Fei Xu
Journal:  J Org Chem       Date:  2015-07-02       Impact factor: 4.354

6.  Enantioselective amine-catalyzed [4+2] annulations of allenoates and oxo-dienes: an asymmetric synthesis of dihydropyrans.

Authors:  Xiaojun Wang; Tong Fang; Xiaofeng Tong
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-27       Impact factor: 15.336

7.  Development of a formal catalytic asymmetric [4+2] addition of ethyl-2,3-butadienoate with acyclic enones.

Authors:  Kumar Dilip Ashtekar; Richard J Staples; Babak Borhan
Journal:  Org Lett       Date:  2011-10-04       Impact factor: 6.005

8.  Enantioselective intramolecular formal [2 + 4] annulation of acrylates and α,β-unsaturated imines catalyzed by amino acid derived phosphines.

Authors:  Zhichao Jin; Ruojie Yang; Yu Du; Bhoopendra Tiwari; Rakesh Ganguly; Yonggui Robin Chi
Journal:  Org Lett       Date:  2012-06-07       Impact factor: 6.005

9.  A computational study: reactivity difference between phosphine- and amine-catalyzed cycloadditions of allenoates and enones.

Authors:  Gou-Tao Huang; Timm Lankau; Chin-Hui Yu
Journal:  J Org Chem       Date:  2014-02-04       Impact factor: 4.354

10.  Amine-catalyzed coupling of allenic esters to alpha,beta-unsaturated carbonyls.

Authors:  Catherine A Evans; Scott J Miller
Journal:  J Am Chem Soc       Date:  2003-10-15       Impact factor: 15.419
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