Journal ArticleDOI
Conjugate addition reactions of chiral (E)-crotylsilanes: application to an asymmetric [3 + 2] cyclopentane annulation
Reads0
Chats0
TLDR
In this paper, a cyclopentanoid was constructed by an initial 1,4-addition followed by a 1,2-silyl migration and a final cyclization step involving the derived boron enolate.Abstract:
Functionalized (E)-crotysilanes 1 undergo Lewis acid promoted conjugate addition reactions with α-substituted enals and methyl vinyl ketone 2 to produce tetrasubstituted cyclopentanes 3 with high levels of diastereoselection. The reaction is believed to proceed by an initial 1,4-addition which is followed by a 1,2-silyl migration and a final cyclization step involving the derived boron enolate resulting in the construction of the cyclopentanoid productread more
Citations
More filters
Journal ArticleDOI
Stereochemical Control in Organic-Synthesis Using Silicon-Containing Compounds
Journal ArticleDOI
Organocatalytic Enantioselective Cascade Michael-Aldol Condensation Reactions : Efficient Assembly of Densely Functionalized Chiral Cyclopentenes
Journal ArticleDOI
Catalytic Enantioselective Carboannulation with Allylsilanes
TL;DR: The first catalytic asymmetric carboannulation with allylsilanes is presented and functionalized cyclopentanes containing a quaternary carbon center are derived from alkylidene oxindole, coumarin, and malonate substrates with high stereoselectivity.
Journal ArticleDOI
Asymmetric synthesis of tetrahydrofurans by diastereoselective [3+2] cycloaddition of allylsilanes with α-keto esters bearing an optically active cyclitol as a chiral auxiliary
TL;DR: Tin (IV) chloride mediated cycloadditions of allylsilanes with optically active α-keto esters derived from L-quebrachitol afforded tetrahydrofuran derivatives via 1,2-silyl migration with high level of diastereoselectivity.
Journal ArticleDOI
Cycloadditions of allylsilances. Part 10. Stereoselective Construction of Ring Systems by Cycloaddition Reactions of allyltriisopropylsilance
TL;DR: Allyltriisopropylsilane is a useful reagent for the stereoselective construction of various ring systems by Lewis acid promoted formal cycloaddition reactions as mentioned in this paper.
Related Papers (5)
Five-membered ring annulation via propargyl- and allylsilanes
Diastereoselective Reactions of Chiral Allyl and Allenyl Silanes with Activated C:X .pi.-Bonds
Craig E. Masse,James S. Panek +1 more