Abstract
Ynolates have been synthesized via the thermally-induced cleavage of ester dianions. The key intermediates, ester dianions, were generated from α-bromocarboxylic acid ester enolates via lithium halogen exchange. α,α-Dibromocarboxylic acid ester also gives lithium amide free ynolates by addition of tert-BuLi. The reactions of ynolates, generated by this novel and convenient method, with aldehydes to give β-lactons are discussed.
| Original language | English |
|---|---|
| Pages (from-to) | 2411-2422 |
| Number of pages | 12 |
| Journal | Tetrahedron |
| Volume | 54 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - Mar 12 1998 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
Novel synthesis of ynolates via the cleavage of ester dianions : α-bromo and α,α-dibromo esters as precursors. / Shindo, Mitsuru; Sato, Yusuke; Shishido, Kozo.
In: Tetrahedron, Vol. 54, No. 11, 12.03.1998, p. 2411-2422.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Novel synthesis of ynolates via the cleavage of ester dianions
T2 - α-bromo and α,α-dibromo esters as precursors
AU - Shindo, Mitsuru
AU - Sato, Yusuke
AU - Shishido, Kozo
PY - 1998/3/12
Y1 - 1998/3/12
N2 - Ynolates have been synthesized via the thermally-induced cleavage of ester dianions. The key intermediates, ester dianions, were generated from α-bromocarboxylic acid ester enolates via lithium halogen exchange. α,α-Dibromocarboxylic acid ester also gives lithium amide free ynolates by addition of tert-BuLi. The reactions of ynolates, generated by this novel and convenient method, with aldehydes to give β-lactons are discussed.
AB - Ynolates have been synthesized via the thermally-induced cleavage of ester dianions. The key intermediates, ester dianions, were generated from α-bromocarboxylic acid ester enolates via lithium halogen exchange. α,α-Dibromocarboxylic acid ester also gives lithium amide free ynolates by addition of tert-BuLi. The reactions of ynolates, generated by this novel and convenient method, with aldehydes to give β-lactons are discussed.
UR - http://www.scopus.com/inward/record.url?scp=0032510257&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0032510257&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(98)00006-4
DO - 10.1016/S0040-4020(98)00006-4
M3 - Article
AN - SCOPUS:0032510257
VL - 54
SP - 2411
EP - 2422
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 11
ER -