Abstract
The title reactions of sterically crowded 2-oxazolidone derivatives with achiral aldehydes in the presence of zinc dust were found to give various 2,3-syn-aldols as major products (at most, 2,3-syn:2,3-anti=98:2). While a 2,3-syn-3,4-syn-aldol could be similarly produced in a highly stereoselective manner, application of the explored reaction to asymmetric synthesis of optically active 2,3-syn-aldols was found to be unpromising.
| Original language | English |
|---|---|
| Pages (from-to) | 6629-6632 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 28 |
| Issue number | 52 |
| DOIs | |
| Publication status | Published - Jan 1 1987 |
| Externally published | Yes |
Fingerprint
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
A highly stereoselective synthesis of aldols employing the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes. / Ito, Yoshio; Terashima, Shiro.
In: Tetrahedron Letters, Vol. 28, No. 52, 01.01.1987, p. 6629-6632.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - A highly stereoselective synthesis of aldols employing the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes
AU - Ito, Yoshio
AU - Terashima, Shiro
PY - 1987/1/1
Y1 - 1987/1/1
N2 - The title reactions of sterically crowded 2-oxazolidone derivatives with achiral aldehydes in the presence of zinc dust were found to give various 2,3-syn-aldols as major products (at most, 2,3-syn:2,3-anti=98:2). While a 2,3-syn-3,4-syn-aldol could be similarly produced in a highly stereoselective manner, application of the explored reaction to asymmetric synthesis of optically active 2,3-syn-aldols was found to be unpromising.
AB - The title reactions of sterically crowded 2-oxazolidone derivatives with achiral aldehydes in the presence of zinc dust were found to give various 2,3-syn-aldols as major products (at most, 2,3-syn:2,3-anti=98:2). While a 2,3-syn-3,4-syn-aldol could be similarly produced in a highly stereoselective manner, application of the explored reaction to asymmetric synthesis of optically active 2,3-syn-aldols was found to be unpromising.
UR - http://www.scopus.com/inward/record.url?scp=0001439535&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0001439535&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(00)96931-4
DO - 10.1016/S0040-4039(00)96931-4
M3 - Article
AN - SCOPUS:0001439535
VL - 28
SP - 6629
EP - 6632
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 52
ER -