Details
| Original language | English |
|---|---|
| Pages (from-to) | 501-507 |
| Number of pages | 7 |
| Journal | Liebigs Annalen |
| Volume | 1995 |
| Issue number | 3 |
| Publication status | Published - 23 Feb 1995 |
| Externally published | Yes |
Abstract
Silyl‐substituted 4‐alken‐1‐ols cyclize in the presence of a wide range of electrophilic reagents to give substituted tetra‐hydrofurans. The silyl group accelerates ring closure by its β‐effect and its position determines the efficiency of stereo‐control. Thus, a vinylic silyl group as in 1, 3‐9 gives mixtures of 2,5‐disubstituted tetrahydrofurans 2, 10‐21, favoring formation of the trans isomer. In contrast, an allylic silyl group as in 28‐30 exerts a high degree of stereocontrol, generally affording 2,3‐trans‐disubstituted tetrahydrofurans 31‐36.
Keywords
- Allylsilanes, Cyclization, stereocontrolled, Tetrahydrofurans, formation of, Vinylsilanes
ASJC Scopus subject areas
- Chemistry(all)
- General Chemistry
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In: Liebigs Annalen, Vol. 1995, No. 3, 23.02.1995, p. 501-507.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Electrophile‐induced cyclizations of silyl‐substituted 4‐alken‐1‐ols
AU - Adiwidjaja, Gunadi
AU - Flörke, H.
AU - Kirschning, Andreas
AU - Schauman, Ernst
PY - 1995/2/23
Y1 - 1995/2/23
N2 - Silyl‐substituted 4‐alken‐1‐ols cyclize in the presence of a wide range of electrophilic reagents to give substituted tetra‐hydrofurans. The silyl group accelerates ring closure by its β‐effect and its position determines the efficiency of stereo‐control. Thus, a vinylic silyl group as in 1, 3‐9 gives mixtures of 2,5‐disubstituted tetrahydrofurans 2, 10‐21, favoring formation of the trans isomer. In contrast, an allylic silyl group as in 28‐30 exerts a high degree of stereocontrol, generally affording 2,3‐trans‐disubstituted tetrahydrofurans 31‐36.
AB - Silyl‐substituted 4‐alken‐1‐ols cyclize in the presence of a wide range of electrophilic reagents to give substituted tetra‐hydrofurans. The silyl group accelerates ring closure by its β‐effect and its position determines the efficiency of stereo‐control. Thus, a vinylic silyl group as in 1, 3‐9 gives mixtures of 2,5‐disubstituted tetrahydrofurans 2, 10‐21, favoring formation of the trans isomer. In contrast, an allylic silyl group as in 28‐30 exerts a high degree of stereocontrol, generally affording 2,3‐trans‐disubstituted tetrahydrofurans 31‐36.
KW - Allylsilanes
KW - Cyclization, stereocontrolled
KW - Tetrahydrofurans, formation of
KW - Vinylsilanes
UR - http://www.scopus.com/inward/record.url?scp=84867405555&partnerID=8YFLogxK
U2 - 10.1002/jlac.199519950369
DO - 10.1002/jlac.199519950369
M3 - Article
AN - SCOPUS:84867405555
VL - 1995
SP - 501
EP - 507
JO - Liebigs Annalen
JF - Liebigs Annalen
SN - 0947-3440
IS - 3
ER -