Enantioselective desymmetrization of meso-N-(heteroarenesulfonyl)aziridines with TMSN3 catalyzed by chiral Lewis acids

Authors :: Nakamura, Shuichi
Hayashi, Masashi
Kamada, Yasutoshi
Sasaki, Ryosuke
Hiramatsu, Yuichi
Shibata, Norio
Toru, Takeshi
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Jul2010, Vol. 51 Issue 29, p3820-3823. 4p.
Publication Year :: 2010
Abstract: Abstract: A catalytic enantioselective desymmetrization of meso-N-(heteroarenesulfonyl)aziridines with TMSN3 using chiral Lewis acids afforded products with high enantioselectivity. As proof of the utility of this procedure, the precursor of selective κ-opioid agonist (1S,2S)-(−)-U-50,488 was synthesized. [Copyright &y& Elsevier]

Subjects :: *AZIRIDINES
*CHIRALITY
*LEWIS acids
*AMINES
*CATALYSTS
*OPIOIDS
*ASYMMETRIC synthesis

Language :: English
ISSN :: 00404039
Volume :: 51
Issue :: 29
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 51810493
Full Text :: https://doi.org/10.1016/j.tetlet.2010.05.065

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