Abstract
Asymmetric C-C bond formation via the diastereoselective aza-Claisen rearrangement of N-allylketene N,O-acetal 4 is described. The starting materials, allylic alkylating agent 1 and optically pure oxazoline 2, are easily prepared and, in a one-pot procedure, generate rearranged oxazolines 5 in 52-94% diastereomeric excess. The overall chemical yields for 2 → 5 range from 51 to 78%. The aza-Claisen rearrangement (4 → 5) proceeds with excellent N,O-acetal face selectivity and with good to excellent chair selectivity. Hydrolysis of rearranged oxazoline 5 completes an enantioselective synthesis of 3-substituted pent-4-enoic acids.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 5769-5775 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 50 |
| Issue number | 26 |
| State | Published - 1985 |
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Cite this
Enantioselective preparation of 3-substituted-4-pentenoic acids via the claisen rearrangement. / Kurth, Mark J.; Decker, Owen H W.
In: Journal of Organic Chemistry, Vol. 50, No. 26, 1985, p. 5769-5775.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Enantioselective preparation of 3-substituted-4-pentenoic acids via the claisen rearrangement
AU - Kurth, Mark J.
AU - Decker, Owen H W
PY - 1985
Y1 - 1985
N2 - Asymmetric C-C bond formation via the diastereoselective aza-Claisen rearrangement of N-allylketene N,O-acetal 4 is described. The starting materials, allylic alkylating agent 1 and optically pure oxazoline 2, are easily prepared and, in a one-pot procedure, generate rearranged oxazolines 5 in 52-94% diastereomeric excess. The overall chemical yields for 2 → 5 range from 51 to 78%. The aza-Claisen rearrangement (4 → 5) proceeds with excellent N,O-acetal face selectivity and with good to excellent chair selectivity. Hydrolysis of rearranged oxazoline 5 completes an enantioselective synthesis of 3-substituted pent-4-enoic acids.
AB - Asymmetric C-C bond formation via the diastereoselective aza-Claisen rearrangement of N-allylketene N,O-acetal 4 is described. The starting materials, allylic alkylating agent 1 and optically pure oxazoline 2, are easily prepared and, in a one-pot procedure, generate rearranged oxazolines 5 in 52-94% diastereomeric excess. The overall chemical yields for 2 → 5 range from 51 to 78%. The aza-Claisen rearrangement (4 → 5) proceeds with excellent N,O-acetal face selectivity and with good to excellent chair selectivity. Hydrolysis of rearranged oxazoline 5 completes an enantioselective synthesis of 3-substituted pent-4-enoic acids.
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UR - http://www.scopus.com/inward/citedby.url?scp=0001072811&partnerID=8YFLogxK
M3 - Article
VL - 50
SP - 5769
EP - 5775
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 26
ER -