Details
| Original language | English |
|---|---|
| Pages (from-to) | 1081-1085 |
| Number of pages | 5 |
| Journal | Tetrahedron Asymmetry |
| Volume | 20 |
| Issue number | 9 |
| Publication status | Published - 22 Apr 2009 |
Abstract
The Diels-Alder cycloaddition of the di-P-stereogenic dienophile (SP,SP)-1 leads to novel di-P-stereogenic norbornene derivatives and proceeds with moderate diastereoselectivity in the absence of a catalyst. In the presence of TiCl4, however, the diastereoselectivity was raised to 9:1. The major diastereoisomer has been characterized crystallographically. The separation of the diastereomeric cycloadducts was possible by fractional crystallization in the presence of (-)-O,O-dibenzoyltartaric acid monohydrate.
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
- Chemistry(all)
- Inorganic Chemistry
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In: Tetrahedron Asymmetry, Vol. 20, No. 9, 22.04.2009, p. 1081-1085.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Asymmetric Diels-Alder cycloaddition of a di-P-stereogenic dienophile with cyclopentadiene
AU - Vinokurov, Nikolai
AU - Michal Pietrusiewicz, K.
AU - Butenschön, Holger
N1 - Funding information: This research was kindly supported by the Gottlieb Daimler and Karl Benz-Foundation (doctoral fellowship to N.V.) and by the Deutsche Forschungsgemeinschaft.
PY - 2009/4/22
Y1 - 2009/4/22
N2 - The Diels-Alder cycloaddition of the di-P-stereogenic dienophile (SP,SP)-1 leads to novel di-P-stereogenic norbornene derivatives and proceeds with moderate diastereoselectivity in the absence of a catalyst. In the presence of TiCl4, however, the diastereoselectivity was raised to 9:1. The major diastereoisomer has been characterized crystallographically. The separation of the diastereomeric cycloadducts was possible by fractional crystallization in the presence of (-)-O,O-dibenzoyltartaric acid monohydrate.
AB - The Diels-Alder cycloaddition of the di-P-stereogenic dienophile (SP,SP)-1 leads to novel di-P-stereogenic norbornene derivatives and proceeds with moderate diastereoselectivity in the absence of a catalyst. In the presence of TiCl4, however, the diastereoselectivity was raised to 9:1. The major diastereoisomer has been characterized crystallographically. The separation of the diastereomeric cycloadducts was possible by fractional crystallization in the presence of (-)-O,O-dibenzoyltartaric acid monohydrate.
UR - http://www.scopus.com/inward/record.url?scp=65549094476&partnerID=8YFLogxK
U2 - 10.1016/j.tetasy.2009.03.022
DO - 10.1016/j.tetasy.2009.03.022
M3 - Article
AN - SCOPUS:65549094476
VL - 20
SP - 1081
EP - 1085
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 9
ER -