Ruthenium-BINAP Catalyzed Alcohol C-H tert-Prenylation via 1,3-Enyne Transfer Hydrogenation: Beyond Stoichiometric Carbanions in Enantioselective Carbonyl Propargylation

被引：79

作者：

Nguyen, Khoa D. ^{[1
]}

Herkommer, Daniel ^{[1
]}

Krische, Michael J. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 16期

关键词：

MEDIATED ALLYLATION REACTION; STEREOSELECTIVE-SYNTHESIS; ALLYLIC TRICHLOROSILANES; QUATERNARY STEREOCENTERS; HOMOALLYLIC ALCOHOLS; ALDEHYDES; REAGENTS; FUNCTIONALIZATION; CROTYLATION; TITANOCENE;

D O I：

10.1021/jacs.6b02279

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The chiral ruthenium complex formed in situ from (TFA)(2)Ru(CO)(PPh3)(2) and (R)-BINAP is found to catalyze the enantioselective C-C coupling of diverse primary alcohols with the 1,3-enyne, TMSC CC(Me)=CH2, to form secondary homopropargyl alcohols bearing gem-dimethyl groups. All reagents for this byproduct-free coupling are inexpensive and commercially available, making this protocol a practical alternative to stoichiometric carbanions in enantioselective carbonyl reverse prenylation.

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页码：5238 / 5241

页数：4

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