Abstract
Starting from the enantiomerically pure monoterpenes (+)‐pulegone (3), (+)‐limonene (7), (−)‐β‐pinene (9), (+)‐ and (−)‐camphor (13) or (+)‐cholestenone (11) the chiral alcohols 4, 5, 6, 8, 10, 12, 14, 15, 16, 17 et 18 were prepared; their acrylates II underwent a TiCl4‐promoted Diels‐Alder addition to cyclopentadiene Scheme 3, Table giving in a predictable manner either the (2R)‐ or the (2S)‐adducts III with 63 to 88% asymmetric induction.
| Original language | German |
|---|---|
| Pages (from-to) | 2802-2807 |
| Number of pages | 6 |
| Journal | Helvetica Chimica Acta |
| Volume | 64 |
| Issue number | 8 |
| DOIs | |
| State | Published - 1981 |
| Externally published | Yes |
ASJC Scopus subject areas
- Catalysis
- Biochemistry
- Drug Discovery
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
Cite this
Asymmetric induction in Diels‐Alder reactions to acrylates derived from chiral sec‐alcohols. Preliminary communication. / Oppolzer, Wolfgang; Kurth, Mark; Reichlin, Daniel; Chapuis, Christian; Mohnhaupt, Martin; Moffatt, Frank.
In: Helvetica Chimica Acta, Vol. 64, No. 8, 1981, p. 2802-2807.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Asymmetric induction in Diels‐Alder reactions to acrylates derived from chiral sec‐alcohols. Preliminary communication
AU - Oppolzer, Wolfgang
AU - Kurth, Mark
AU - Reichlin, Daniel
AU - Chapuis, Christian
AU - Mohnhaupt, Martin
AU - Moffatt, Frank
PY - 1981
Y1 - 1981
N2 - Starting from the enantiomerically pure monoterpenes (+)‐pulegone (3), (+)‐limonene (7), (−)‐β‐pinene (9), (+)‐ and (−)‐camphor (13) or (+)‐cholestenone (11) the chiral alcohols 4, 5, 6, 8, 10, 12, 14, 15, 16, 17 et 18 were prepared; their acrylates II underwent a TiCl4‐promoted Diels‐Alder addition to cyclopentadiene Scheme 3, Table giving in a predictable manner either the (2R)‐ or the (2S)‐adducts III with 63 to 88% asymmetric induction.
AB - Starting from the enantiomerically pure monoterpenes (+)‐pulegone (3), (+)‐limonene (7), (−)‐β‐pinene (9), (+)‐ and (−)‐camphor (13) or (+)‐cholestenone (11) the chiral alcohols 4, 5, 6, 8, 10, 12, 14, 15, 16, 17 et 18 were prepared; their acrylates II underwent a TiCl4‐promoted Diels‐Alder addition to cyclopentadiene Scheme 3, Table giving in a predictable manner either the (2R)‐ or the (2S)‐adducts III with 63 to 88% asymmetric induction.
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UR - http://www.scopus.com/inward/citedby.url?scp=0000075203&partnerID=8YFLogxK
U2 - 10.1002/hlca.19810640841
DO - 10.1002/hlca.19810640841
M3 - Article
AN - SCOPUS:0000075203
VL - 64
SP - 2802
EP - 2807
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
SN - 0018-019X
IS - 8
ER -