Abstract
The nucleophilic allylation of various chiral auxiliaries derived glyoxylic oxime ethers was studied. The use of allyltributylstannane in the presence of a Lewis acid and triallylaluminum provided the corresponding homoallylic amines in high chemical yields (up to 89%) and excellent stereoselectivities (up to >99%). The stereochemical bias of the allylation is proposed.
| Original language | English |
|---|---|
| Pages (from-to) | 7816-7822 |
| Number of pages | 7 |
| Journal | Tetrahedron |
| Volume | 63 |
| Issue number | 33 |
| DOIs | |
| Publication status | Published - 2007 Aug 13 |
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Keywords
- Allylation
- Chiral auxiliary
- Glyoxylic oxime ether
- Triallylaluminum
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
On the scope of diastereoselective allylation of various chiral glyoxylic oxime ethers with allyltributylstannane in the presence of a Lewis acid and triallylaluminum. / Kulkarni, Neelesh A.; Yao, Ching-Fa; Chen, Kwunmin.
In: Tetrahedron, Vol. 63, No. 33, 13.08.2007, p. 7816-7822.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - On the scope of diastereoselective allylation of various chiral glyoxylic oxime ethers with allyltributylstannane in the presence of a Lewis acid and triallylaluminum
AU - Kulkarni, Neelesh A.
AU - Yao, Ching-Fa
AU - Chen, Kwunmin
PY - 2007/8/13
Y1 - 2007/8/13
N2 - The nucleophilic allylation of various chiral auxiliaries derived glyoxylic oxime ethers was studied. The use of allyltributylstannane in the presence of a Lewis acid and triallylaluminum provided the corresponding homoallylic amines in high chemical yields (up to 89%) and excellent stereoselectivities (up to >99%). The stereochemical bias of the allylation is proposed.
AB - The nucleophilic allylation of various chiral auxiliaries derived glyoxylic oxime ethers was studied. The use of allyltributylstannane in the presence of a Lewis acid and triallylaluminum provided the corresponding homoallylic amines in high chemical yields (up to 89%) and excellent stereoselectivities (up to >99%). The stereochemical bias of the allylation is proposed.
KW - Allylation
KW - Chiral auxiliary
KW - Glyoxylic oxime ether
KW - Triallylaluminum
UR - http://www.scopus.com/inward/record.url?scp=34347267212&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=34347267212&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2007.05.091
DO - 10.1016/j.tet.2007.05.091
M3 - Article
VL - 63
SP - 7816
EP - 7822
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 33
ER -