Literature DB >> 19890378

Saucy-Marbet Rearrangements of Alkynyl Halides in the Synthesis of Highly Enantiomerically Enriched Allenyl Halides.

Yu Tang1, Lichun Shen, Becky J Dellaria, Richard P Hsung.   

Abstract

A stereospecific Saucy-Marbet rearrangement of alkynyl halides is described here. These rearrangements provide an entry to highly enantiomerically enriched allenyl bromides and chlorides through excellent chirality transfer and the reservation of optical integrity of alkynyl halides.

Entities:  

Year:  2008        PMID： 19890378      PMCID： PMC2598747          DOI： 10.1016/j.tetlet.2008.08.089

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  29 in total

1.  A formal total synthesis of (+)-zincophorin. Observation of an unusual urea-directed Stork-Crabtree hydrogenation.

Authors:  Zhenlei Song; Richard P Hsung
Journal:  Org Lett       Date:  2007-05-05       Impact factor: 6.005

2.  Boron-mediated stereoselective syntheses of gamma,gamma-disubstituted allenamides.

Authors:  Christopher J T Hyland; Louis S Hegedus
Journal:  J Org Chem       Date:  2005-10-14       Impact factor: 4.354

Review 3.  Catalytic asymmetric organozinc additions to carbonyl compounds.

Authors:  L Pu; H B Yu
Journal:  Chem Rev       Date:  2001-03       Impact factor: 60.622

4.  De novo chiral amino alcohols in catalyzing asymmetric additions to aryl aldehydes.

Authors:  Jian Huang; James C Ianni; Jennifer E Antoline; Richard P Hsung; Marisa C Kozlowski
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

5.  Rhodium-catalyzed intramolecular [4 + 2] cycloadditions of alkynyl halides.

Authors:  Woo-Jin Yoo; Anna Allen; Karine Villeneuve; William Tam
Journal:  Org Lett       Date:  2005-12-22       Impact factor: 6.005

6.  Syntheses of 2,5-disubstituted dihydrofurans from gamma-substituted chiral allenamides.

Authors:  Craig R Berry; Richard P Hsung; Jennifer E Antoline; Matthew E Petersen; Rameshkumar Challeppan; Jessica A Nielson
Journal:  J Org Chem       Date:  2005-05-13       Impact factor: 4.354

7.  Highly stereoselective Saucy-Marbet rearrangement using chiral ynamides. Synthesis of highly substituted chiral homoallenyl alcohols.

Authors:  Michael O Frederick; Richard P Hsung; Robert H Lambeth; Jason A Mulder; Michael R Tracey
Journal:  Org Lett       Date:  2003-07-24       Impact factor: 6.005

8.  Gold-catalyzed hydroarylation of allenes: a highly regioselective carbon-carbon bond formation producing six-membered rings.

Authors:  Toshiaki Watanabe; Shinya Oishi; Nobutaka Fujii; Hiroaki Ohno
Journal:  Org Lett       Date:  2007-10-09       Impact factor: 6.005

9.  Palladium-catalyzed multistep reactions involving ring closure of 2-iodophenoxyallenes and ring opening of bicyclic alkenes.

Authors:  Kanniyappan Parthasarathy; Masilamani Jeganmohan; Chien-Hong Cheng
Journal:  Org Lett       Date:  2006-02-16       Impact factor: 6.005

10.  A strategy for the synthesis of 2,3-disubstituted indoles starting from N-(o-halophenyl)allenamides.

Authors:  Haruhiko Fuwa; Makoto Sasaki
Journal:  Org Biomol Chem       Date:  2007-06-19       Impact factor: 3.876
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  4 in total

1.  Asymmetric synthesis of allenyl oxindoles and spirooxindoles by a catalytic enantioselective Saucy-Marbet Claisen rearrangement.

Authors:  Trung Cao; Joshua Deitch; Elizabeth C Linton; Marisa C Kozlowski
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-27       Impact factor: 15.336

2.  Copper(II)- and palladium(II)-catalyzed enantioselective Claisen rearrangement of allyloxy- and propargyloxy-indoles to quaternary oxindoles and spirocyclic lactones.

Authors:  Trung Cao; Elizabeth C Linton; Joshua Deitch; Simon Berritt; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2012-12-04       Impact factor: 4.354

3.  Allylic and allenic halide synthesis via NbCl(5)- and NbBr(5)-mediated alkoxide rearrangements.

Authors:  P C Ravikumar; Lihua Yao; Fraser F Fleming
Journal:  J Org Chem       Date:  2009-10-02       Impact factor: 4.354

Review 4.  Allenamides: a powerful and versatile building block in organic synthesis.

Authors:  Ting Lu; Zhenjie Lu; Zhi-Xiong Ma; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2013-04-04       Impact factor: 60.622
  4 in total

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