Journal ArticleDOI
Tandem Intramolecular Silylformylation−Crotylsilylation: Highly Efficient Synthesis of Polyketide Fragments
TLDR
A new dihydrosilane alcoholysis reaction has been developed, leading to a highly efficient sequence of reactions establishing up to three new stereocenters with good-to-excellent diastereoselectivity.Abstract:
Polyketide fragments may be rapidly and efficiently assembled in the tandem intramolecular silylformylation−crotylsilylation of alkenes and alkynes. The reactions establish up to three new stereocenters with good-to-excellent diastereoselectivity, and the use of the reaction in an iterative sense is demonstrated. In addition, a new dihydrosilane alcoholysis reaction has been developed, leading to a highly efficient sequence.read more
Citations
More filters
Journal ArticleDOI
Catalytic Asymmetric Silane Alcoholysis: Practical Access to Chiral Silanes
TL;DR: A new asymmetric synthesis of chiral silanes with good to excellent stereoselectivity at silicon is developed and the application of this methodology to the tandem silylformylation-allylsilylation of alkynes has been demonstrated.
Journal ArticleDOI
Recent advances in the use of temporary silicon tethers in metal-mediated reactions.
TL;DR: This tutorial review describes the use of temporary silicon tethers in metal-mediated organic reactions, a strategy which although well-established in traditional organic synthesis is still a blossoming field in the organometallic arena.
Journal ArticleDOI
Recent Progress in Asymmetric Synthesis and Application of Difunctionalized Silicon‐Stereogenic Silanes
TL;DR: In this article, an overview of difunctionalized silanes containing asymmetrically substituted silicon centers is presented, with a special focus on recent achievements in the field of silicon-stereogenic N,O-silanes, new mechanistic aspects of stereocontrolled nucleophilic substitutions are also discussed.
Journal ArticleDOI
Development of β-keto 1,3-dithianes as versatile intermediates for organic synthesis
TL;DR: beta-Keto 1,3-dithianes can be generated by the double conjugate addition of dithiols to propargylic ketones, esters and aldehydes in excellent yields and can be converted to a range of functionalised oxygen-containing heterocycles that can be used in natural product synthesis.
Journal ArticleDOI
Potassium tert-butoxide-catalyzed dehydrogenative Si-O coupling: reactivity pattern and mechanism of an underappreciated alcohol protection.
TL;DR: A comprehensive survey of common silanes provides a reliable tool for the predictability of their reactivity under defined reaction conditions and a transition state for the enantiospecific Si-O coupling step is suggested rationalizing the observed frontside attack and thus retention at the silicon atom.
References
More filters
Journal ArticleDOI
The condensation reaction of trichlorosilane with allylic chlorides catalyzed by copper salts in the presence of a tertiary amine
N. Furuya,T. Sukawa +1 more
TL;DR: In this paper, allyl trichlorosilane undergoes a smooth reaction at room temperature with allyl chloride, β-methallyl chloride, crotyl chloride and α-methyltaphyll chloride to give the corresponding allyltrichloro-silane in excellent yields in the presence of an equimolar amount of a tertiary amine and a catalytic amount of cuprous chloride.
Journal ArticleDOI
Tandem Intramolecular Alkyne Silylformylation-Allylsilylation: A Case of Remote 1,5-Asymmetric Induction.
TL;DR: With remarkable efficiency, this new reaction provides, through remote 1,5-asymmetric induction, anti-1,5 diols that are useful synthons for polyol synthesis (see scheme; Hacac=acetylacetone).