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

Magorzata Kosior; Monika Asztemborska; Janusz Jurczak

doi:10.1055/s-2003-44372

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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 Kosior^a, Monika Asztemborska^b, 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;

Abstract

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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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Referenzen

References

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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

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