A New Chiral Masked Form of Glyoxal Diimine

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Title:A New Chiral Masked Form of Glyoxal Diimine
Creators:
Martelli, Gianluca
Savoia, Diego
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 68, 8, pp. 1531-1540
Uncontrolled Keywords:Diastereoselective synthesis, Substitutions, Rearrangements, Amines, Lithium, Alkyllithium reagents, Retro reactions, Additions, Imines

Abstract

(3<i>R</i>,4<i>R</i>,5<i>R</i>,6<i>R</i>)-3,6-Diphenyl-<i>N</i>,<i>N'</i>-bis[(<i>S</i>)-1-phenylethyl]octa-1,7-diene-4,5-diamine, by treatment with organolithium reagents RLi in controlled experimental conditions, underwent rearrangement and/or substitution of one or two branched allyl(s) by the R group(s). Hence, this diene behaves as a masked form of the chiral glyoxal diimine from that it is prepared, allowing the preparation of C<sub>1</sub>-symmetric 1,2-disubstituted 1,2-diamines, which are generally not available by the direct addition of organometallic reagents to the diimine, and C<sub>2</sub>-symmetric 1,2-diamines with good diastereoselectivities. <p>

Title:A New Chiral Masked Form of Glyoxal Diimine
Creators:
Martelli, Gianluca
Savoia, Diego
Uncontrolled Keywords:Diastereoselective synthesis, Substitutions, Rearrangements, Amines, Lithium, Alkyllithium reagents, Retro reactions, Additions, Imines
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:68
Number:8
Page Range:pp. 1531-1540
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20031531UNSPECIFIED
ID Code:2135
Item Type:Article
Deposited On:06 Feb 2009 17:15
Last Modified:06 Feb 2009 16:16

Citation

Martelli, Gianluca; Savoia, Diego (2003) A New Chiral Masked Form of Glyoxal Diimine. Collection of Czechoslovak Chemical Communications, 68 (8). pp. 1531-1540. ISSN 0010-0765

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