Details
| Original language | English |
|---|---|
| Pages (from-to) | 1117-1122 |
| Number of pages | 6 |
| Journal | SYNLETT |
| Volume | 33 |
| Issue number | 12 |
| Early online date | 17 Feb 2022 |
| Publication status | Published - 23 Mar 2022 |
Abstract
Here we present our work on a Kiyooka aldol protocol for the stereoselective synthesis of tertiary alcohols. In the obtained products, three oxygenated carbon atoms that could further be differentiated flank the chiral tertiary alcohol. This methodology can be applied to simplearomatic or aliphatic aldehydes and more complex substrates bearing a chiral center in the and/or -position. For complex substrates, an unexpected dependency between stereoselectivity and double-bond geometry of the ketene acetal was observed. Furthermore, applications in or towards the synthesis of natural products are presented.
Keywords
- aldol reaction, double-bond geometry, ketene acetal, stereoselective synthesis, tertiary alcohols
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: SYNLETT, Vol. 33, No. 12, 23.03.2022, p. 1117-1122.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Chiral Polyoxygenated Tertiary Alcohols through Kiyooka Aldol Reaction
AU - Lücke, Daniel
AU - Kalesse, Markus
N1 - Funding Information: This work was supported by the Deutsche Forschungsgemeinschaft (KA 913/25-1).DeutcheFochunggemeinschaftKA913/251)
PY - 2022/3/23
Y1 - 2022/3/23
N2 - Here we present our work on a Kiyooka aldol protocol for the stereoselective synthesis of tertiary alcohols. In the obtained products, three oxygenated carbon atoms that could further be differentiated flank the chiral tertiary alcohol. This methodology can be applied to simplearomatic or aliphatic aldehydes and more complex substrates bearing a chiral center in the and/or -position. For complex substrates, an unexpected dependency between stereoselectivity and double-bond geometry of the ketene acetal was observed. Furthermore, applications in or towards the synthesis of natural products are presented.
AB - Here we present our work on a Kiyooka aldol protocol for the stereoselective synthesis of tertiary alcohols. In the obtained products, three oxygenated carbon atoms that could further be differentiated flank the chiral tertiary alcohol. This methodology can be applied to simplearomatic or aliphatic aldehydes and more complex substrates bearing a chiral center in the and/or -position. For complex substrates, an unexpected dependency between stereoselectivity and double-bond geometry of the ketene acetal was observed. Furthermore, applications in or towards the synthesis of natural products are presented.
KW - aldol reaction
KW - double-bond geometry
KW - ketene acetal
KW - stereoselective synthesis
KW - tertiary alcohols
UR - http://www.scopus.com/inward/record.url?scp=85127424172&partnerID=8YFLogxK
U2 - 10.1055/a-1775-7590
DO - 10.1055/a-1775-7590
M3 - Article
AN - SCOPUS:85127424172
VL - 33
SP - 1117
EP - 1122
JO - SYNLETT
JF - SYNLETT
SN - 0936-5214
IS - 12
ER -