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Synthesis 2004(1): 87-91  
DOI: 10.1055/s-2003-44372
PAPER
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Reaction of Buta-1,3-diene with Chiral Derivatives of Glyoxylic­ Acid: Effective Route to Optically Pure 2-Substituted 3,6-Dihydro-2 H -pyrans

Magorzata Kosiora, Monika Asztemborskab, Janusz Jurczak*a,c
a Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland
b Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
c Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
Fax: +48(22)8230944; e-Mail: jjurczak@chem.uw.edu.pl;
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Publication History

Received 12 September 2003
Publication Date:
09 December 2003 (online)

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Abstract

The influence of Lewis acids on the diastereoselectivity of [4+2] cycloaddition of buta-1,3-diene (4) to N-glyoxyloyl-(2R)-bornane-10,2-sultam (6a) and (R)-8-phenylmenthyl glyoxylate (6b) was investigated and found to have high levels of asymmetric induction. The highest asymmetric induction (ca. 100% de) was obtained for the reaction of 4 with 6b carried out in toluene and in the presence of chelating Lewis acids (SnCl4, TiCl4).

Key words

catalysis - chiral auxiliaries - Diels-Alder reactions - Lewis acids - stereoselectivity

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8

Kwiatkowski P., Kosior M., Asztemborska M., Jurczak J.; unpublished results