Literature DB >> 23923982

Enantioselective catalytic transannular ketone-ene reactions.

Naomi S Rajapaksa1, Eric N Jacobsen.   

Abstract

Highly enantio- and diastereoselective transannular ketone-ene reactions are catalyzed by a new chromium(III) triflate tridentate Schiff base complex. Electronically unactivated keto-olefins undergo heteroene reactions at ambient temperature to afford enantioenriched bicyclic alcohols, common structural motifs in natural products. The kinetic resolution of a configurationally stable planar-chiral cyclodecenone is also described.

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Year:  2013        PMID： 23923982      PMCID： PMC3799808          DOI： 10.1021/ol401968m

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


  28 in total

1.  Asymmetric total synthesis of (-)-merrilactone A: use of a bulky protecting group as long-range stereocontrolling element.

Authors:  Masayuki Inoue; Takaaki Sato; Masahiro Hirama
Journal:  Angew Chem Int Ed Engl       Date:  2006-07-17       Impact factor: 15.336

2.  Origin of diastereoselectivity in the tandem oxy-Cope/Claisen/ene reaction: experimental and theoretical studies of the ring inversion mechanism.

Authors:  Effiette L O Sauer; James Hooper; Tom Woo; Louis Barriault
Journal:  J Am Chem Soc       Date:  2007-01-27       Impact factor: 15.419

3.  Highly enantioselective organocatalytic carbonyl-ene reaction with strongly acidic, chiral Brønsted acids as efficient catalysts.

Authors:  Magnus Rueping; Thomas Theissmann; Alexander Kuenkel; René M Koenigs
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Highly Enantio- and Diastereoselective Hetero-Diels-Alder Reactions Catalyzed by New Chiral Tridentate Chromium(III) Catalysts.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-08       Impact factor: 15.336

5.  Enantioselective intramolecular aldol addition/dehydration reaction of a macrocyclic diketone: synthesis of the musk odorants (R)-muscone and (R,Z)-5-muscenone.

Authors:  Oliver Knopff; Jérôme Kuhne; Charles Fehr
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  Catalyst-controlled diastereoselective hetero-Diels-Alder reactions.

Authors:  Guy D Joly; Eric N Jacobsen
Journal:  Org Lett       Date:  2002-05-16       Impact factor: 6.005

7.  Total synthesis and bioactivity of an unnatural enantiomer of merrilactone a: development of an enantioselective desymmetrization strategy.

Authors:  Masayuki Inoue; Nayoung Lee; Satoshi Kasuya; Takaaki Sato; Masahiro Hirama; Miyako Moriyama; Yoshiyasu Fukuyama
Journal:  J Org Chem       Date:  2007-03-14       Impact factor: 4.354

8.  Asymmetric platinum group metal-catalyzed carbonyl-ene reactions: carbon-carbon bond formation versus isomerization.

Authors:  Simon Doherty; Julian G Knight; Catherine H Smyth; Ross W Harrington; William Clegg
Journal:  J Org Chem       Date:  2006-12-22       Impact factor: 4.354

9.  Catalytic, asymmetric transannular aldolizations: total synthesis of (+)-hirsutene.

Authors:  Carley L Chandler; Benjamin List
Journal:  J Am Chem Soc       Date:  2008-05-03       Impact factor: 15.419

10.  The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas.

Authors:  Matthew L Clarke; Charlotte E S Jones; Marcia B France
Journal:  Beilstein J Org Chem       Date:  2007-09-14       Impact factor: 2.883
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  4 in total

1.  Cooperative Hydrogen-Bond-Donor Catalysis with Hydrogen Chloride Enables Highly Enantioselective Prins Cyclization Reactions.

Authors:  Dennis A Kutateladze; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2021-11-23       Impact factor: 15.419

2.  A [6+4]-cycloaddition adduct is the biosynthetic intermediate in streptoseomycin biosynthesis.

Authors:  Kai Biao Wang; Wen Wang; Bo Zhang; Xin Wang; Yu Chen; Hong Jie Zhu; Yong Liang; Ren Xiang Tan; Hui Ming Ge
Journal:  Nat Commun       Date:  2021-04-07       Impact factor: 14.919

3.  Transannular Approach to 2,3-Dihydropyrrolo[1,2-b]isoquinolin-5(1H)-ones through Brønsted Acid-Catalyzed Amidohalogenation.

Authors:  Estefanía Capel; Javier Luis-Barrera; Ana Sorazu; Uxue Uria; Liher Prieto; Efraím Reyes; Luisa Carrillo; Jose L Vicario
Journal:  J Org Chem       Date:  2022-07-26       Impact factor: 4.198

4.  Catalytic, transannular carbonyl-olefin metathesis reactions.

Authors:  Paul S Riehl; Daniel J Nasrallah; Corinna S Schindler
Journal:  Chem Sci       Date:  2019-09-25       Impact factor: 9.825
  4 in total

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