+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Catalytic enantioselective desymmetrization of COT-monoepoxide. Maximum deviation from coplanarity for an S(N)2'-cuprate alkylation



Catalytic enantioselective desymmetrization of COT-monoepoxide. Maximum deviation from coplanarity for an S(N)2'-cuprate alkylation



Organic Letters 5(11): 1971-1974



[reaction: see text] The first alkylative and enantioselective ring-opening of COT-monoepoxide (1) without the occurrence of any ring-contraction-isomerization by the use of in situ-formed organocuprates is reported. Because of the particular geometric constraint of compound 1, this work reports the largest deviation from coplanarity between the pi-orbital of the double bond and the sigma-bond connecting the leaving group ever observed for an S(N)2'-cuprate alkylation.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 048464322

Download citation: RISBibTeXText

PMID: 12762699

DOI: 10.1021/ol034554t


Related references

Catalytic Enantioselective Desymmetrization of Norbornenoquinones via C(sp 2 )-H Alkylation. Organic Letters 18(23): 6160-6163, 2016

Enantioselective desymmetrization of prochiral 1,3-dinitropropanes via organocatalytic allylic alkylation. Chemical Communications 50(1): 121-123, 2014

Catalytic enantioselective intermolecular desymmetrization of azetidines. Journal of the American Chemical Society 137(18): 5895-5898, 2015

Catalytic enantioselective intermolecular desymmetrization of 3-substituted oxetanes. Angewandte Chemie 52(26): 6685-6688, 2013

Catalytic enantioselective desymmetrization of meso-N-acylaziridines with TMSCN. Journal of the American Chemical Society 127(32): 11252-3, 2005

A new catalytic and enantioselective desymmetrization of symmetrical methylidene cycloalkene oxides. Organic Letters 2(7): 933-936, 2000

Catalytic Enantioselective Desymmetrization Reactions to All-Carbon Quaternary Stereocenters. Chemical Reviews 116(12): 7330-7396, 2016

Highly enantioselective synthesis of α,α-dialkylmalonates by phase-transfer catalytic desymmetrization. Journal of the American Chemical Society 133(13): 4924-4929, 2011

Desymmetrization-like catalytic enantioselective fluorination of malonates and its application to pharmaceutically attractive molecules. Angewandte Chemie 47(1): 164-168, 2008

Catalytic enantioselective desymmetrization of meso cyclic anhydrides via iridium-catalyzed hydrogenation. Organic Letters 15(7): 1740-1743, 2013

Highly enantioselective catalytic desymmetrization of cyclic anhydrides with modified cinchona alkaloids. Abstracts of Papers American Chemical Society 222(1-2): ORGN192, 2001

A catalytic and enantioselective desymmetrization of meso cyclic allylic bisdiethylphosphates with organozinc reagents. Angewandte Chemie 42(2): 234-236, 2003

Catalytic enantioselective total syntheses of bakkenolides I, J, and S: application of a carbene-catalyzed desymmetrization. Organic Letters 12(12): 2830-2833, 2010

Catalytic enantioselective desymmetrization of meso-diamines: a dual small-molecule catalysis approach. Journal of the American Chemical Society 133(37): 14538-14541, 2011

Catalytic enantioselective desymmetrization of meso-glutaric anhydrides using a stable Ni2-Schiff base catalyst. Organic Letters 14(5): 1358-1361, 2012