Abstract
The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.
| Original language | English |
|---|---|
| Pages (from-to) | 9345-9347 |
| Number of pages | 3 |
| Journal | Tetrahedron Letters |
| Volume | 45 |
| Issue number | 51 |
| DOIs | |
| Publication status | Published - 2004 Dec 13 |
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Keywords
- Diastereoselective
- Glyoxylate-ene reaction
- Stereogenic center
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile. / Pan, Jia Fu; Venkatesham, Uppala; Chen, Kwunmin.
In: Tetrahedron Letters, Vol. 45, No. 51, 13.12.2004, p. 9345-9347.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile
AU - Pan, Jia Fu
AU - Venkatesham, Uppala
AU - Chen, Kwunmin
PY - 2004/12/13
Y1 - 2004/12/13
N2 - The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.
AB - The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.
KW - Diastereoselective
KW - Glyoxylate-ene reaction
KW - Stereogenic center
UR - http://www.scopus.com/inward/record.url?scp=8844233484&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=8844233484&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2004.10.121
DO - 10.1016/j.tetlet.2004.10.121
M3 - Article
AN - SCOPUS:8844233484
VL - 45
SP - 9345
EP - 9347
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 51
ER -