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Wu Y.,Key Laboratory of Drug Targeting of Education Ministry | Li L.,Key Laboratory of Drug Targeting of Education Ministry | Li H.,Key Laboratory of Drug Targeting of Education Ministry | Gao L.,Key Laboratory of Drug Targeting of Education Ministry | And 6 more authors.
Organic Letters | Year: 2014

A regioselective nucleophilic addition to 3-geminal bis(silyl) N-acyl pyridinium has been described. Geminal bis(silane) shows contrasting roles that lead to different regioselectivities for the addition of different nucleophiles: its steric effect dominates to favor 1,6-addition of alkyl, vinyl, and aryl organometallic reagents; its directing effect dominates to favor 1,2-addition of less sterically demanding alkynyl Grignard reagents. © 2014 American Chemical Society.


Gao L.,Key Laboratory of Drug Targeting of Education Ministry | Lin X.,Key Laboratory of Drug Targeting of Education Ministry | Lei J.,Key Laboratory of Drug Targeting of Education Ministry | Song Z.,Key Laboratory of Drug Targeting of Education Ministry | And 3 more authors.
Organic Letters | Year: 2012

Bissilyl enal, prepared by a Mannich reaction of 3,3-bissilyl aldehyde with formaldehyde, has proven to be a useful linchpin in an efficient three-component coupling process. The reaction features a [1,4]-Brook rearrangement to generate the silylallyl anion, which adopts a predominant endo-orientation and can undergo addition to electrophiles in a regio- and stereoselective manner, giving various E-vinylsilane species in good yields. © 2011 American Chemical Society.


Sun X.,Key Laboratory of Drug Targeting of Education Ministry | Lei J.,Key Laboratory of Drug Targeting of Education Ministry | Sun C.,Key Laboratory of Drug Targeting of Education Ministry | Song Z.,Key Laboratory of Drug Targeting of Education Ministry | And 2 more authors.
Organic Letters | Year: 2012

The [1,5]-anion relay/[2,3]-Wittig rearrangement of 3,3-bis(silyl) enol allyl ethers has been developed. This reaction provides an efficient method to synthesize versatile vinyl bissilanes, which can be transformed into trisubstituted vinylsilanes through a [1,4]-Brook rearrangement/alkylation protocol using a wide range of electrophiles. © 2012 American Chemical Society.


Xu Y.,Key Laboratory of Drug Targeting of Education Ministry | Yin Z.,Key Laboratory of Drug Targeting of Education Ministry | Lin X.,Key Laboratory of Drug Targeting of Education Ministry | Gan Z.,Key Laboratory of Drug Targeting of Education Ministry | And 4 more authors.
Organic Letters | Year: 2015

A regioselective 1,4-hydroiodination of dienyl alcohols has been developed using trimethylsilyl iodide as Lewis acid and iodide source. A range of homoallylic alcohols containing a multisubstituted Z-alkene was synthesized with good to excellent configurational control. The approach was applied in sequential hydroiodination/Prins cyclization to afford multisubstituted tetrahydropyrans diastereoselectively. © 2015 American Chemical Society.


Lin X.,Key Laboratory of Drug Targeting of Education Ministry | Ye X.,Key Laboratory of Drug Targeting of Education Ministry | Sun X.,Key Laboratory of Drug Targeting of Education Ministry | Zhang Y.,Key Laboratory of Drug Targeting of Education Ministry | And 3 more authors.
Organic Letters | Year: 2014

A [1,5]-anion relay has been achieved in 3,3-bis(silyl) benzyl enol ether. Deprotonation at the sterically more accessible benzyl position triggers an intramolecular proton transfer to generate the thermodynamically more stable 3,3-bis(silyl) allyloxy lithium. This endo-oriented allyl anion is stable at -78 C and undergoes diastereoselective syn-addition at the γ-position with aldehydes and ketones to give monobenzyl-substituted 1,2-diols. © 2014 American Chemical Society.


Li L.,Key Laboratory of Drug Targeting of Education Ministry | Ye X.,Key Laboratory of Drug Targeting of Education Ministry | Wu Y.,Key Laboratory of Drug Targeting of Education Ministry | Gao L.,Key Laboratory of Drug Targeting of Education Ministry | And 4 more authors.
Organic Letters | Year: 2013

3,3-Bis(silyl) silyl enol ethers have been shown to exhibit predominantly Sakurai reactivity, rather than Mukaiyama aldol reactivity, in their Lewis acid promoted reactions with acetals. Starting from a geminal bis(silyl) moiety consisting of two different silyl groups, such as SiMe3 and SiMe 2Ph, the SiMe3 is selectively eliminated to give monoprotected E- vinylsilyl diols with good to excellent syn- diastereoselectivity. This reaction also underpinned a synthesis of the nematocidal oxylipid from Notheia anomala, demonstrating the attractive bifunctionality of geminal bis(silanes). © 2013 American Chemical Society.


Sun C.,Key Laboratory of Drug Targeting of Education Ministry | Sun C.,University of Sichuan | Zhang Y.,Key Laboratory of Drug Targeting of Education Ministry | Zhang Y.,University of Sichuan | And 5 more authors.
Organic Letters | Year: 2014

An intramolecular [1,4]-S- to O-silyl migration has been used to form silyl enol ethers with Z-configurational control. The silyl migration also creates a new anion center at sulfur, which can subsequently react with electrophiles to generate Z-silyl enol ethers with diverse thioether linkages. The synthetic utility of this pathway was demonstrated by modifying the Z-silyl enol ethers with aldehydes via a Mukaiyama aldol reaction or Prins cyclization to generate functionalized organosulfur compounds. © 2014 American Chemical Society.

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