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Literature DB >> 21830779

Enantioselective conjugate allylation of cyclic enones.

Douglass F Taber¹, David A Gerstenhaber, James F Berry.

Abstract

Enantioselective organocatalytic 1,2-allylation of a cyclic enone followed by anionic oxy-Cope rearrangement delivered the ketone as a mixture of diastereomers. This appears to be a general method for the net enantioselective conjugate allylation of cyclic enones.

Entities: CellLine Chemical Species

Mesh：

Substances：
Hydrocarbons, Cyclic

Year: 2011 PMID： 21830779 PMCID： PMC3237403 DOI： 10.1021/jo2013753

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

21 in total

1. Asymmetric conjugate addition to alpha-halo enones: dramatic effect of styrene on the enantioselectivity.

Authors: Kangying Li; Alexandre Alexakis
Journal: Angew Chem Int Ed Engl Date: 2006-11-20 Impact factor: 15.336

2. Highly enantioselective allylation of alpha-ketoesters catalyzed by N,N'-dioxide-In(III) complexes.

Authors: Ke Zheng; Bo Qin; Xiaohua Liu; Xiaoming Feng
Journal: J Org Chem Date: 2007-10-06 Impact factor: 4.354

3. Regiodivergent 1,4 versus 1,6 asymmetric copper-catalyzed conjugate addition.

Authors: Hélène Hénon; Marc Mauduit; Alexandre Alexakis
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

4. Synthesis of 2,7-Cyclofarnesol and 2,7-Cyclogeranylgeraniol: Prenylogs of beta-Cyclogeraniol.

Authors: Robert M. Coates; Alan Qingwu Jin
Journal: J Org Chem Date: 1997-10-17 Impact factor: 4.354

5. Synthesis of isohasubanan alkaloids via enantioselective ketone allylation and discovery of an unexpected rearrangement.

Authors: Daniel K Nielsen; Laura L Nielsen; Spencer B Jones; Lawrence Toll; Matthew C Asplund; Steven L Castle
Journal: J Org Chem Date: 2009-02-06 Impact factor: 4.354

6. A three-step route to a tricyclic steroid precursor.

Authors: Douglass F Taber; Ritesh B Sheth
Journal: J Org Chem Date: 2008-09-25 Impact factor: 4.354

7. Rhodium-catalyzed intramolecular hydroacylation of 5- and 6-alkynals: convenient synthesis of alpha-alkylidenecycloalkanones and cycloalkenones.

Authors: Kenzo Takeishi; Koudai Sugishima; Kaori Sasaki; Ken Tanaka
Journal: Chemistry Date: 2004-11-05 Impact factor: 5.236

8. Catalytic enantioselective allylboration of ketones.

Authors: Reiko Wada; Kounosuke Oisaki; Motomu Kanai; Masakatsu Shibasaki
Journal: J Am Chem Soc Date: 2004-07-28 Impact factor: 15.419

9. Catalytic enantioselective Hosomi-Sakurai conjugate allylation of cyclic unsaturated ketoesters.

Authors: Manami Shizuka; Marc L Snapper
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

10. Copper-catalyzed asymmetric conjugate addition of trialkylaluminium reagents to trisubstituted enones: construction of chiral quaternary centers.

Authors: Magali Vuagnoux-d'Augustin; Alexandre Alexakis
Journal: Chemistry Date: 2007 Impact factor: 5.236

4 in total