Literature DB >> 22780578

Diastereoselective synthesis of seven-membered-ring trans-alkenes from dienes and aldehydes by silylene transfer.

Margaret A Greene1, Michel Prévost, Joshua Tolopilo, K A Woerpel.   

Abstract

Silver-catalyzed silylene transfer to alkenes forms vinylsilacyclopropanes regioselectively. These allylic silanes undergo additions to aldehydes to form seven-membered-ring trans-alkenes with high diastereoselectivity. The high reactivity of the trans-alkenes is evidenced by their formal [1,3]-sigmatropic rearrangement reactions and the rapid additions of oxygen-hydrogen bonds across the carbon-carbon double bonds.

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Year:  2012        PMID： 22780578      PMCID： PMC3437758          DOI： 10.1021/ja305713v

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  12 in total

1.  Control of Stereochemistry by sigma-Participation of a Silyl Group. A Novel Method for Diastereoselective Polyol Synthesis.

Authors:  Keiji Tanino; Naoei Yoshitani; Fumiko Moriyama; Isao Kuwajima
Journal:  J Org Chem       Date:  1997-06-27       Impact factor: 4.354

2.  Strained silacycles in organic synthesis: a new reagent for the enantioselective allylation of aldehydes.

Authors:  James W A Kinnaird; Pui Yee Ng; Katsumi Kubota; Xiaolun Wang; James L Leighton
Journal:  J Am Chem Soc       Date:  2002-07-10       Impact factor: 15.419

3.  Origins of stereoselectivity in strain-release allylations.

Authors:  Xiyun Zhang; Kendall N Houk; James L Leighton
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-28       Impact factor: 15.336

4.  An unconventional approach to the enantioselective synthesis of caryophylloids.

Authors:  Oleg V Larionov; E J Corey
Journal:  J Am Chem Soc       Date:  2008-02-16       Impact factor: 15.419

5.  Electrophilic fluorocyclization of allyl silanes.

Authors:  Susan C Wilkinson; Oscar Lozano; Marie Schuler; Maria C Pacheco; Roger Salmon; Véronique Gouverneur
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Stereoselective multimodal transformations of planar chiral 9-membered diallylic amides.

Authors:  Katsuhiko Tomooka; Masaki Suzuki; Maki Shimada; Runyan Ni; Kazuhiro Uehara
Journal:  Org Lett       Date:  2011-08-23       Impact factor: 6.005

7.  Silylene-mediated polarity reversal of dienoates: additions of dienoates to aldehydes at the δ-position to form trans-dioxasilacyclononenes.

Authors:  Christian C Ventocilla; K A Woerpel
Journal:  J Am Chem Soc       Date:  2010-12-17       Impact factor: 15.419

8.  Stereoselective Synthesis of (Z)- and (E)-Allylic Silanes by Copper-Mediated Substitution Reactions of Allylic Carbamates with Grignard Reagents.

Authors: 
Journal:  J Org Chem       Date:  2000-03-24       Impact factor: 4.354

9.  Insertions of silylenes into vinyl epoxides: diastereoselective synthesis of functionalized, optically active trans-dioxasilacyclooctenes.

Authors:  Michel Prévost; K A Woerpel
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

10.  Mechanism of di-tert-butylsilylene transfer from a silacyclopropane to an alkene.

Authors:  Tom G Driver; K A Woerpel
Journal:  J Am Chem Soc       Date:  2003-09-03       Impact factor: 15.419
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  4 in total

1.  Carboalumination of Seven-Membered-Ring trans-Alkenes.

Authors:  Margaret A Greene; Yudong Liu; Jillian R Sanzone; K A Woerpel
Journal:  Org Lett       Date:  2020-09-17       Impact factor: 6.005

2.  Studies on the Stability and Stabilization of trans-Cyclooctenes through Radical Inhibition and Silver (I) Metal Complexation.

Authors:  Yinzhi Fang; Joshua C Judkins; Samantha J Boyd; Christopher W Am Ende; Katarina Rohlfing; Zhen Huang; Yixin Xie; Douglas S Johnson; Joseph M Fox
Journal:  Tetrahedron       Date:  2019-05-26       Impact factor: 2.457

3.  Flow Photochemical Syntheses of trans-Cyclooctenes and trans-Cycloheptenes Driven by Metal Complexation.

Authors:  Jessica E Pigga; Joseph M Fox
Journal:  Isr J Chem       Date:  2019-10-10       Impact factor: 3.333

4.  Photochemical syntheses, transformations, and bioorthogonal chemistry of trans-cycloheptene and sila trans-cycloheptene Ag(i) complexes.

Authors:  Yinzhi Fang; Han Zhang; Zhen Huang; Samuel L Scinto; Jeffrey C Yang; Christopher W Am Ende; Olga Dmitrenko; Douglas S Johnson; Joseph M Fox
Journal:  Chem Sci       Date:  2018-01-08       Impact factor: 9.825
  4 in total

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