Details
| Original language | English |
|---|---|
| Pages (from-to) | 7721-7729 |
| Number of pages | 9 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 10 |
| Issue number | 38 |
| Publication status | Published - 14 Oct 2012 |
Abstract
The Yamamoto aldol reaction is a vinylogous aldol reaction that relies on bulky aluminium-based Lewis acids. These activate both the aldehyde as well as become part of the enolate moiety. The report discloses the first detailed study on the substrate-controlled Yamamoto aldol reaction in which 2,3-syn and 2,3-anti disubstituted aldehydes serve as the stereodirecting elements. The "size" of the substituent in the β-position strongly determines the facial selectivity of enolate addition to the aldehyde. Large substituents favour formation of 1,3-syn diols while slim alkynyl groups preferentially lead to 1,3-anti products.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic and Biomolecular Chemistry, Vol. 10, No. 38, 14.10.2012, p. 7721-7729.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Substrate-controlled stereoselectivity in the Yamamoto aldol reaction
AU - Schläger, Nadin
AU - Kirschning, Andreas
PY - 2012/10/14
Y1 - 2012/10/14
N2 - The Yamamoto aldol reaction is a vinylogous aldol reaction that relies on bulky aluminium-based Lewis acids. These activate both the aldehyde as well as become part of the enolate moiety. The report discloses the first detailed study on the substrate-controlled Yamamoto aldol reaction in which 2,3-syn and 2,3-anti disubstituted aldehydes serve as the stereodirecting elements. The "size" of the substituent in the β-position strongly determines the facial selectivity of enolate addition to the aldehyde. Large substituents favour formation of 1,3-syn diols while slim alkynyl groups preferentially lead to 1,3-anti products.
AB - The Yamamoto aldol reaction is a vinylogous aldol reaction that relies on bulky aluminium-based Lewis acids. These activate both the aldehyde as well as become part of the enolate moiety. The report discloses the first detailed study on the substrate-controlled Yamamoto aldol reaction in which 2,3-syn and 2,3-anti disubstituted aldehydes serve as the stereodirecting elements. The "size" of the substituent in the β-position strongly determines the facial selectivity of enolate addition to the aldehyde. Large substituents favour formation of 1,3-syn diols while slim alkynyl groups preferentially lead to 1,3-anti products.
UR - http://www.scopus.com/inward/record.url?scp=84874891148&partnerID=8YFLogxK
U2 - 10.1039/c2ob26185e
DO - 10.1039/c2ob26185e
M3 - Article
AN - SCOPUS:84874891148
VL - 10
SP - 7721
EP - 7729
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 38
ER -