Regioselectivity control in a ruthenium-catalyzed cycloisomerization of diyne-ols

被引：42

作者：

Trost, BM ^{[1
]}

Rudd, MT ^{[1
]}

Costa, MG ^{[1
]}

Lee, PI ^{[1
]}

Pomerantz, AE ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 23期

关键词：

D O I：

10.1021/ol048351w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ruthenium-catalyzed cycloisomerization of diynes containing one silyl alkyne and one propargyl alcohol yields 2-silyl-[6H]-pyrans instead of the expected unsaturated acylsilanes except when additional conjugation of a aromatic ring is present at the delta-position. Under certain conditions, a facile ruthenium-catalyzed isomerization of the product takes place as well. This regioselectivity of the cyclization can be controlled by the choice of solvent system. DFT calculations confirm the expected greater stability of the silyl-pyrans relative to the acylsilanes.

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页码：4235 / 4238

页数：4

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