Literature DB >> 15255688

Tin(IV) chloride-chiral pyrogallol derivatives as new Lewis acid-assisted chiral Brønsted acids for enantioselective polyene cyclization.

Keiko Kumazawa1, Kazuaki Ishihara, Hisashi Yamamoto.   

Abstract

[reaction: see text] New Lewis acid-assisted Brønsted acids (LBAs), tin(IV) chloride-2,6-dialkoxyphenols, serve as artificial cyclases for biomimetic polyene cyclization. For example, the enantioselective cyclization of 4-(homogeranyl)toluene using tin(IV) chloride-2,6-di[(1'R,2'R)-trans-2'-(3' ',5' '-xylyl)cyclohexanoxy]phenol gave a trans-fused tricyclic compound with 85% ee.

Entities:  

Year:  2004        PMID： 15255688     DOI： 10.1021/ol049126h

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

Review 1.  A case study in biomimetic total synthesis: polyolefin carbocyclizations to terpenes and steroids.

Authors:  Ryan A Yoder; Jeffrey N Johnston
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

2.  Asymmetric oxidative cation/olefin cyclization of polyenes: evidence for reversible cascade cyclization.

Authors:  Charles A Mullen; Alison N Campbell; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Syntheses of (+)-30-epi-, (-)-6-epi-, (±)-6,30-epi-13,14-Didehydroxyisogarcinol and (±)-6,30-epi-Garcimultiflorone A Utilizing Highly Diastereoselective, Lewis Acid-Controlled Cyclizations.

Authors:  Jonathan H Boyce; Vincent Eschenbrenner-Lux; John A Porco
Journal:  J Am Chem Soc       Date:  2016-10-27       Impact factor: 15.419

4.  Development of a new Lewis base-tolerant chiral LBA and its application to catalytic asymmetric protonation reaction.

Authors:  Cheol Hong Cheon; Tatsushi Imahori; Hisashi Yamamoto
Journal:  Chem Commun (Camb)       Date:  2010-08-23       Impact factor: 6.222

5.  Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A.

Authors:  Joseph J Topczewski; John G Kodet; David F Wiemer
Journal:  J Org Chem       Date:  2011-01-12       Impact factor: 4.354

6.  Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes.

Authors:  Zhonglin Tao; Kevin A Robb; Kuo Zhao; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2018-03-06       Impact factor: 15.419

7.  Catalytic platinum-initiated cation-olefin reactions with alkene terminating groups.

Authors:  Joseph G Sokol; Nikki A Cochrane; Jennifer J Becker; Michel R Gagné
Journal:  Chem Commun (Camb)       Date:  2013-04-26       Impact factor: 6.222

8.  Enantioselective Tail-to-Head Cyclizations Catalyzed by Dual-Hydrogen-Bond Donors.

Authors:  Dennis A Kutateladze; Daniel A Strassfeld; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2020-04-03       Impact factor: 15.419

9.  Electrophilic Pt(II) complexes: precision instruments for the initiation of transformations mediated by the cation-olefin reaction.

Authors:  Ryan J Felix; Colleen Munro-Leighton; Michel R Gagné
Journal:  Acc Chem Res       Date:  2014-05-20       Impact factor: 22.384
  9 in total

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