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Literature DB >> 14677957

Catalytic enantioselective iodocyclization of gamma-hydroxy-cis-alkenes.

Sung Ho Kang¹, Sung Bae Lee, Chul Min Park.

Abstract

Enantioselective iodocyclization of gamma-hydroxy-cis-alkenes has been achieved using I2 in the presence of an unprecedented catalyst system generated from (R,R)-t-Bu-salen-Co(II) complex and NCS to produce 2-monosubstituted tetrahydrofurans up to 90% ee. While NCS turned out to be the essential additive, neither (R,R)-salen-Co(II) nor (R,R)-salen-Co(III) by itself is likely to be the active species responsible for the asymmetric intramolecular iodoetherification.

Entities: Chemical

Year: 2003 PMID： 14677957 DOI： 10.1021/ja0369921

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

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Cited

23 in total

1. Copper-catalyzed intramolecular alkene carboetherification: synthesis of fused-ring and bridged-ring tetrahydrofurans.

Authors: Yan Miller; Lei Miao; Azade S Hosseini; Sherry R Chemler
Journal: J Am Chem Soc Date: 2012-07-05 Impact factor: 15.419

2. An organocatalytic asymmetric chlorolactonization.

Authors: Daniel C Whitehead; Roozbeh Yousefi; Arvind Jaganathan; Babak Borhan
Journal: J Am Chem Soc Date: 2010-03-17 Impact factor: 15.419

3. Recent Advances in the Stereoselective Synthesis of Tetrahydrofurans.

Authors: John P Wolfe; Michael B Hay
Journal: Tetrahedron Date: 2007-01-08 Impact factor: 2.457

4. 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

5. Reversing the Regioselectivity of Halofunctionalization Reactions through Cooperative Photoredox and Copper Catalysis.

Authors: Jeremy D Griffin; Cortney L Cavanaugh; David A Nicewicz
Journal: Angew Chem Int Ed Engl Date: 2017-01-20 Impact factor: 15.336

Catalytic enantioselective iodocyclization of gamma-hydroxy-cis-alkenes.

1. Copper-catalyzed intramolecular alkene carboetherification: synthesis of fused-ring and bridged-ring tetrahydrofurans.

2. An organocatalytic asymmetric chlorolactonization.

3. Recent Advances in the Stereoselective Synthesis of Tetrahydrofurans.

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

5. Reversing the Regioselectivity of Halofunctionalization Reactions through Cooperative Photoredox and Copper Catalysis.

6. Terminating platinum-initiated cation-olefin reactions with simple alkenes.

7. Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer.

Review 8. Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.

9. A Cyclization/Oxygenation Scheme for the Conversion of Polyenes into C3-Oxygenated Polycycles.

10. Catalytic enantioselective cyclization and C3-fluorination of polyenes.