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Literature DB >> 23901903

Atom economical, one-pot, three-reaction cascade to novel tricyclic 2,4-dihydro-1H-benzo[f]isochromenes.

Abstract

Reaction of 6-methyl-1-phenylhept-3-yne-2,6-diol with various aldehydes under Lewis acid conditions provides an atom economical, two-component cascade reaction sequence to novel 2,4-dihydro-1H-benzo[f]isochromene compounds. Aliphatic aldehydes as well as electron-deficient and -rich aromatic aldehydes can be used.

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Year: 2013 PMID： 23901903 PMCID： PMC4447333 DOI： 10.1021/ol401600j

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

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References

36 in total

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Authors: Hao Li; Teck-Peng Loh
Journal: Org Lett Date: 2010-06-18 Impact factor: 6.005

2. Enantioselective synthesis of the C18-C25 segment of lasonolide A by an oxonia-cope prins cascade.

Authors: Jackline E Dalgard; Scott D Rychnovsky
Journal: Org Lett Date: 2005-04-14 Impact factor: 6.005

3. 5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans via Prins-type cyclization.

Authors: Satish N Chavre; Hyunah Choo; Joo Hwan Cha; Ae Nim Pae; Kyung Il Choi; Yong Seo Cho
Journal: Org Lett Date: 2006-08-03 Impact factor: 6.005

4. Racemization in Prins cyclization reactions.

Authors: Ramesh Jasti; Scott D Rychnovsky
Journal: J Am Chem Soc Date: 2006-10-18 Impact factor: 15.419

5. Synthesis of 1-aminoisoquinolines by gold(III)-mediated domino reactions from 2-alkynylbenzamides and ammonium acetate.

Authors: Yuhua Long; Zhigang She; Xiaochen Liu; Yu Chen
Journal: J Org Chem Date: 2013-03-01 Impact factor: 4.354

10. Highly efficient and stereocontrolled construction of 3,3'-pyrrolidonyl spirooxindoles via organocatalytic domino Michael/cyclization reaction.

Authors: Xiong-Li Liu; Wen-Yong Han; Xiao-Mei Zhang; Wei-Cheng Yuan
Journal: Org Lett Date: 2013-03-01 Impact factor: 6.005

Atom economical, one-pot, three-reaction cascade to novel tricyclic 2,4-dihydro-1H-benzo[f]isochromenes.

1. A facile method for the synthesis of highly substituted six-membered rings: Mukaiyama-Aldol-Prins cascade reaction.

2. Enantioselective synthesis of the C18-C25 segment of lasonolide A by an oxonia-cope prins cascade.

3. 5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans via Prins-type cyclization.

4. Racemization in Prins cyclization reactions.

5. Synthesis of 1-aminoisoquinolines by gold(III)-mediated domino reactions from 2-alkynylbenzamides and ammonium acetate.

6. Indium-catalyzed construction of polycyclic aromatic hydrocarbon skeletons via dehydration.

7. Stereoselectivity and regioselectivity in the segment-coupling Prins cyclization.

8. Lewis Acid-Promoted Mukaiyama Aldol-Prins (MAP) Cyclizations of Acetals, Ketals, α-Acetoxy Ethers, and Orthoformates.

9. Synthesis of 2,6-disubstituted dihydropyrans via an efficient BiBr(3)-initiated three component, one-pot cascade.

10. Highly efficient and stereocontrolled construction of 3,3'-pyrrolidonyl spirooxindoles via organocatalytic domino Michael/cyclization reaction.