Stereoselective Synthesis of 2-Substituted Pyrrolidines

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Title:Stereoselective Synthesis of 2-Substituted Pyrrolidines
Creators:
Deloisy, Sandrine
Tietgen, Heiko
Kunz, Horst
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 5, pp. 816-828
Uncontrolled Keywords:Homoallylamines, Chiral auxiliaries, Electrophile-induced cyclization, Nornicotine, Alkaloids, Enantioselective reactions, Pyrrolidines, Carbohydrates

Abstract

Using <i>O</i>-pivaloyl protected D-galactopyranosylamine and D-arabinopyranosylamine, (<i>S</i>) or (<i>R</i>) configured α-substituted homoallylamines are synthesized with high diastereoselectivity by reaction of the corresponding aldimines with allyltributylstannane. Electrophile-induced <i>endo</i>-trig-cyclization of these <i>N</i>-glycosylhomoallylamines gave the 2-substituted pyrrolidines of high diastereomeric purity. <p>

Title:Stereoselective Synthesis of 2-Substituted Pyrrolidines
Creators:
Deloisy, Sandrine
Tietgen, Heiko
Kunz, Horst
Uncontrolled Keywords:Homoallylamines, Chiral auxiliaries, Electrophile-induced cyclization, Nornicotine, Alkaloids, Enantioselective reactions, Pyrrolidines, Carbohydrates
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:65
Number:5
Page Range:pp. 816-828
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20000816UNSPECIFIED
ID Code:1682
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Deloisy, Sandrine; Tietgen, Heiko; Kunz, Horst (2000) Stereoselective Synthesis of 2-Substituted Pyrrolidines. Collection of Czechoslovak Chemical Communications, 65 (5). pp. 816-828. ISSN 0010-0765

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