Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 3217-3226 |
| Number of pages | 10 |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| Volume | 2000 |
| Issue number | 19 |
| Early online date | 11 Sep 2000 |
| DOIs | |
| Publication status | Published - 2000 |
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Keywords
- trifluoroethanol
- allylic alcohols
- fragmentation
- benzyloxy
- allyloxy
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Synthesis of α-hydroxy-β,β-difluoro-γ-ketoesters via [3,3]sigmatropic rearrangements. / Broadhurst, Michael; Brown, Samantha J ; Percy, Jonathan; Prime, Michael E .
In: Journal of the Chemical Society, Perkin Transactions 1, Vol. 2000, No. 19, 2000, p. 3217-3226.Research output: Contribution to journal › Article
TY - JOUR
T1 - Synthesis of α-hydroxy-β,β-difluoro-γ-ketoesters via [3,3]sigmatropic rearrangements
AU - Broadhurst, Michael
AU - Brown, Samantha J
AU - Percy, Jonathan
AU - Prime, Michael E
PY - 2000
Y1 - 2000
N2 - Readily available γ,γ-difluorinated allylic alcohols obtained from trifluoroethanol were esterified efficiently. Exposure to strong base (LDA) afforded the ester enolates, in which chelation both controlled configuration and stabilised against fragmentation, which were trapped as their silyl ketene acetals. Rearrangement occurred to afford base-sensitive acid products. Esterification under mild conditions afforded the purifiable methyl esters in which the masked ketone had been released. Educts with either a benzyloxy or an allyloxy group at the α-position could be deprotected releasing the alcohols.
AB - Readily available γ,γ-difluorinated allylic alcohols obtained from trifluoroethanol were esterified efficiently. Exposure to strong base (LDA) afforded the ester enolates, in which chelation both controlled configuration and stabilised against fragmentation, which were trapped as their silyl ketene acetals. Rearrangement occurred to afford base-sensitive acid products. Esterification under mild conditions afforded the purifiable methyl esters in which the masked ketone had been released. Educts with either a benzyloxy or an allyloxy group at the α-position could be deprotected releasing the alcohols.
KW - trifluoroethanol
KW - allylic alcohols
KW - fragmentation
KW - benzyloxy
KW - allyloxy
U2 - 10.1039/B004766J
DO - 10.1039/B004766J
M3 - Article
VL - 2000
SP - 3217
EP - 3226
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
SN - 1472-7781
IS - 19
ER -