Abstract
A chiral auxilliary-based direct aldol reaction is reported. The reactions are catalytic in magnesium salts and are facilitated by silylation with chlorotrimethylsilane. The adducts isolated are in high diastereoselectivity (up to 32:1 dr) and favor the anti-aldol diastereomer B. Reactions are operationally simple and can be run under ambient atmosphere without rigorous exclusion of water. Many of the adducts are highly crystalline and a single diastereomer can be isolated without chromatography.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 392-393 |
| Number of pages | 2 |
| Journal | Journal of the American Chemical Society |
| Volume | 124 |
| Issue number | 3 |
| DOIs | |
| State | Published - Jan 23 2002 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Chemistry(all)
Cite this
Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones. / Evans, David A.; Tedrow, Jason S.; Shaw, Jared T.; Downey, C. Wade.
In: Journal of the American Chemical Society, Vol. 124, No. 3, 23.01.2002, p. 392-393.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones
AU - Evans, David A.
AU - Tedrow, Jason S.
AU - Shaw, Jared T.
AU - Downey, C. Wade
PY - 2002/1/23
Y1 - 2002/1/23
N2 - A chiral auxilliary-based direct aldol reaction is reported. The reactions are catalytic in magnesium salts and are facilitated by silylation with chlorotrimethylsilane. The adducts isolated are in high diastereoselectivity (up to 32:1 dr) and favor the anti-aldol diastereomer B. Reactions are operationally simple and can be run under ambient atmosphere without rigorous exclusion of water. Many of the adducts are highly crystalline and a single diastereomer can be isolated without chromatography.
AB - A chiral auxilliary-based direct aldol reaction is reported. The reactions are catalytic in magnesium salts and are facilitated by silylation with chlorotrimethylsilane. The adducts isolated are in high diastereoselectivity (up to 32:1 dr) and favor the anti-aldol diastereomer B. Reactions are operationally simple and can be run under ambient atmosphere without rigorous exclusion of water. Many of the adducts are highly crystalline and a single diastereomer can be isolated without chromatography.
UR - http://www.scopus.com/inward/record.url?scp=0037160423&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037160423&partnerID=8YFLogxK
U2 - 10.1021/ja0119548
DO - 10.1021/ja0119548
M3 - Article
C2 - 11792206
AN - SCOPUS:0037160423
VL - 124
SP - 392
EP - 393
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 3
ER -