Abstract
We developed the first highly regioselective synthesis of cyclic enol ethers from readily accessible acyclic alkenyl ketones or acyclic alkenyl silyl esters using ring-closing metathesis (RCM). The RCM of acyclic enol silyl ethers was examined using Tebbe reagent 5 or Grubbs catalyst 6 or 7 and successfully proceeded using the second generation Grubbs catalyst 7 to afford the corresponding cyclic enol ethers in high yield (up to 99%, two steps from alkenyl kenone). This process can be applied to syntheses of a variety of cyclic enol ethers in a highly regioselective manner.
| Original language | English |
|---|---|
| Pages (from-to) | 8023-8027 |
| Number of pages | 5 |
| Journal | Tetrahedron Letters |
| Volume | 42 |
| Issue number | 45 |
| DOIs | |
| Publication status | Published - Nov 5 2001 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Highly regioselective synthesis of cyclic enol silyl ethers using ring-closing metathesis. / Okada, Akihiro; Ohshima, Takashi; Shibasaki, Masakatsu.
In: Tetrahedron Letters, Vol. 42, No. 45, 05.11.2001, p. 8023-8027.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Highly regioselective synthesis of cyclic enol silyl ethers using ring-closing metathesis
AU - Okada, Akihiro
AU - Ohshima, Takashi
AU - Shibasaki, Masakatsu
PY - 2001/11/5
Y1 - 2001/11/5
N2 - We developed the first highly regioselective synthesis of cyclic enol ethers from readily accessible acyclic alkenyl ketones or acyclic alkenyl silyl esters using ring-closing metathesis (RCM). The RCM of acyclic enol silyl ethers was examined using Tebbe reagent 5 or Grubbs catalyst 6 or 7 and successfully proceeded using the second generation Grubbs catalyst 7 to afford the corresponding cyclic enol ethers in high yield (up to 99%, two steps from alkenyl kenone). This process can be applied to syntheses of a variety of cyclic enol ethers in a highly regioselective manner.
AB - We developed the first highly regioselective synthesis of cyclic enol ethers from readily accessible acyclic alkenyl ketones or acyclic alkenyl silyl esters using ring-closing metathesis (RCM). The RCM of acyclic enol silyl ethers was examined using Tebbe reagent 5 or Grubbs catalyst 6 or 7 and successfully proceeded using the second generation Grubbs catalyst 7 to afford the corresponding cyclic enol ethers in high yield (up to 99%, two steps from alkenyl kenone). This process can be applied to syntheses of a variety of cyclic enol ethers in a highly regioselective manner.
UR - http://www.scopus.com/inward/record.url?scp=0035813419&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0035813419&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(01)01713-0
DO - 10.1016/S0040-4039(01)01713-0
M3 - Article
AN - SCOPUS:0035813419
VL - 42
SP - 8023
EP - 8027
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 45
ER -