Diastereoselective addition of allyltrimethylsilane to N-glyoxyloyl(2R)- bornane-10,2-sultam. A new synthesis of (S)-1,2-pentanediol

Article abstract of DOI:10.1080/00397919908085920

Addition of allyltrimethylsilane (3) to N-glyoxyloyl-(2R)-bornane-10,2- sultam (4) in the presence of Lewis acid afforded, in high diastereoselectivity, adduct (2'S')-6 which, after recrystallization, was hydrogenated to give optically pure (S)-1,2-pentanediol (1).

Full text of DOI:10.1080/00397919908085920

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Synthetic Communications: An
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Diastereoselective Addition of
Allyltrimethylsilane to N-Glyoxyloyl-
(2R)-bornane-10,2-sultam. A new
synthesis of (S)-1,2-Pentanediol
Katarzyna Kiegiel a , Piotr Prokopowicz b & Janusz Jurczak a
b
a Department of Chemistry, Warsaw University, Pastern,
1,02-093, Warsaw
b Institute of Organic Chemistry, Polish Academy of Sciences,
Kaspnaka 44/52, 01-224, Warsaw, Poland
Published online: 17 Sep 2007.
To cite this article: Katarzyna Kiegiel , Piotr Prokopowicz & Janusz Jurczak (1999):
Diastereoselective Addition of Allyltrimethylsilane to N-Glyoxyloyl-(2R)-bornane-10,2-sultam.
A new synthesis of (S)-1,2-Pentanediol, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 29:22, 3999-4005
To link to this article: http://dx.doi.org/10.1080/00397919908085920
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