Literature DB >> 20387811

Regio- and stereocontrol in rhenium-catalyzed transposition of allylic alcohols.

Aaron T Herrmann1, Tatsuo Saito, Craig E Stivala, Janine Tom, Armen Zakarian.   

Abstract

A hydroxyl group-directed, highly regio- and stereoselective transposition of allylic alcohols based on rhenium catalysis has been developed. The method is suitable for a direct isomerization of acetals into the thermodynamically preferred isomer as long as one of the hydroxyl groups is allylic. This method will expand the scope of rhenium-catalyzed alcohol transpositions for complex molecule synthesis.

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Year:  2010        PMID： 20387811      PMCID： PMC2861154          DOI： 10.1021/ja101673v

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


  7 in total

1.  Approach to the synthesis of cladiell-11-ene-3,6,7-triol.

Authors:  John M Hutchison; Harriet A Lindsay; Silvana S Dormi; Gavin D Jones; David A Vicic; Matthias C McIntosh
Journal:  Org Lett       Date:  2006-08-17       Impact factor: 6.005

2.  A dynamic kinetic resolution of allyl alcohols by the combined use of lipases and [VO(OSiPh3)3].

Authors:  Shuji Akai; Kouichi Tanimoto; Yukiko Kanao; Masahiro Egi; Tomoko Yamamoto; Yasuyuki Kita
Journal:  Angew Chem Int Ed Engl       Date:  2006-04-10       Impact factor: 15.336

3.  Rhenium-catalyzed 1,3-isomerization of allylic alcohols: scope and chirality transfer.

Authors:  Christie Morrill; Gregory L Beutner; Robert H Grubbs
Journal:  J Org Chem       Date:  2006-09-29       Impact factor: 4.354

4.  Regiochemical control in the metal-catalyzed transposition of allylic silyl ethers.

Authors:  Eric C Hansen; Daesung Lee
Journal:  J Am Chem Soc       Date:  2006-06-28       Impact factor: 15.419

5.  Highly selective 1,3-isomerization of allylic alcohols via rhenium oxo catalysis.

Authors:  Christie Morrill; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2005-03-09       Impact factor: 15.419

6.  Rhenium(VII) catalysis of Prins cyclization reactions.

Authors:  Kwanruthai Tadpetch; Scott D Rychnovsky
Journal:  Org Lett       Date:  2008-09-25       Impact factor: 6.005

7.  Symmetric macrocycles by a Prins dimerization and macrocyclization strategy.

Authors:  Michael R Gesinski; Kwanruthai Tadpetch; Scott D Rychnovsky
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005
  7 in total
  10 in total

1.  Studies toward the synthesis of spirolide C: exploration into the formation of the 23-membered all-carbon macrocyclic framework.

Authors:  Craig E Stivala; Zhenhua Gu; Lindsay L Smith; Armen Zakarian
Journal:  Org Lett       Date:  2012-01-19       Impact factor: 6.005

2.  Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction.

Authors:  Scott E Denmark; Zachery D Matesich; Son T Nguyen; Selena Milicevic Sephton
Journal:  J Org Chem       Date:  2017-12-08       Impact factor: 4.354

3.  Re2 O7 -Mediated Dehydrative Cyclization Reactions: Total Synthesis of Herboxidiene and Its 12-Desmethyl Analogue.

Authors:  Tyler M Rohrs; Qi Qin; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-28       Impact factor: 15.336

4.  Unusual Rearrangement-Remercuration Reactions of Allylic Silanols.

Authors:  Someshwar Nagamalla; Ranjeet A Dhokale; Frederick J Seidl; Joel T Mague; Shyam Sathyamoorthi
Journal:  Org Chem Front       Date:  2021-08-03       Impact factor: 5.456

5.  Dynamic kinetic resolution of transient hemiketals: a strategy for the desymmetrisation of prochiral oxetanols.

Authors:  Alexander Sandvoß; Henning Maag; Constantin G Daniliuc; Dieter Schollmeyer; Johannes M Wahl
Journal:  Chem Sci       Date:  2022-05-04       Impact factor: 9.969

6.  The regio- and stereospecific intermolecular dehydrative alkoxylation of allylic alcohols catalyzed by a gold(I) N-heterocyclic carbene complex.

Authors:  Paramita Mukherjee; Ross A Widenhoefer
Journal:  Chemistry       Date:  2013-01-24       Impact factor: 5.236

7.  Cascade approach to stereoselective polycyclic ether formation: epoxides as trapping agents in the transposition of allylic alcohols.

Authors:  Youwei Xie; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-22       Impact factor: 15.336

8.  Novel carbocationic rearrangements of 1-styrylpropargyl alcohols.

Authors:  Christine Basmadjian; Fan Zhang; Laurent Désaubry
Journal:  Beilstein J Org Chem       Date:  2015-06-15       Impact factor: 2.883

9.  Re2O7-catalyzed reaction of hemiacetals and aldehydes with O-, S-, and C-nucleophiles.

Authors:  Wantanee Sittiwong; Michael W Richardson; Charles E Schiaffo; Thomas J Fisher; Patrick H Dussault
Journal:  Beilstein J Org Chem       Date:  2013-07-30       Impact factor: 2.883

10.  Gold-catalyzed 1,3-transposition of ynones.

Authors:  Roohollah Kazem Shiroodi; Mohammad Soltani; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2014-07-02       Impact factor: 15.419
  10 in total

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