Literature DB >> 19702255

Asymmetric synthesis of aminochromanes via intramolecular indium-mediated allylation of chiral hydrazones.

Debasis Samanta1, Robert B Kargbo, Gregory R Cook.   

Abstract

The asymmetric intramolecular indium-mediated cyclization reaction delivers chromanes with excellent diastereoselectivity (68-91% yield, dr >99:1). The reaction was efficient for aryl substrates with both electron-withdrawing and -donating groups. Carboxylic acid additives were found to be necessary for optimal reaction.

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Year:  2009        PMID： 19702255      PMCID： PMC6280656          DOI： 10.1021/jo901195g

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  24 in total

1.  Selective reduction of terminal alkynes to alkenes by indium metal.

Authors:  B C Ranu; J Dutta; S K Guchhait
Journal:  J Org Chem       Date:  2001-08-10       Impact factor: 4.354

2.  Cardioselective antiischemic ATP-sensitive potassium channel (KATP) openers. 5. Identification of 4-(N-aryl)-substituted benzopyran derivatives with high selectivity.

Authors:  G C Rovnyak; S Z Ahmed; C Z Ding; S Dzwonczyk; F N Ferrara; W G Humphreys; G J Grover; D Santafianos; K S Atwal; A J Baird; L G McLaughlin; D E Normandin; P G Sleph; S C Traeger
Journal:  J Med Chem       Date:  1997-01-03       Impact factor: 7.446

3.  A stereoselective intramolecular 1,3-dipolar nitrone cycloaddition for the synthesis of substituted chromanes.

Authors:  Qian Zhao; Fusen Han; Donna L Romero
Journal:  J Org Chem       Date:  2002-05-17       Impact factor: 4.354

4.  The catalytic asymmetric Mannich-type reactions in aqueous media.

Authors:  Shū Kobayashi; Tomoaki Hamada; Kei Manabe
Journal:  J Am Chem Soc       Date:  2002-05-22       Impact factor: 15.419

5.  Cyclization of 1-bromo-2,7- and 1-bromo-2,8-enynes mediated by indium.

Authors:  Phil Ho Lee; Sundae Kim; Kooyeon Lee; Dong Seomoon; Hyunseok Kim; Seokju Lee; Misook Kim; Mijeong Han; Kwanghyun Noh; Tom Livinghouse
Journal:  Org Lett       Date:  2004-12-23       Impact factor: 6.005

6.  Intermolecular alkyl radical addition to chiral N-acylhydrazones mediated by manganese carbonyl.

Authors:  G K Friestad; J Qin
Journal:  J Am Chem Soc       Date:  2001-10-10       Impact factor: 15.419

7.  Highly diastereoselective mannich-type reactions of chiral N-acylhydrazones.

Authors:  Mikkel F Jacobsen; Liviu Ionita; Troels Skrydstrup
Journal:  J Org Chem       Date:  2004-07-09       Impact factor: 4.354

8.  Optically active aromatic and heteroaromatic alpha-amino acids by a one-pot catalytic enantioselective addition of aromatic and heteroaromatic C-H bonds to alpha-imino esters.

Authors:  Steen Saaby; Pau Bayón; Pompiliu S Aburel; Karl Anker Jørgensen
Journal:  J Org Chem       Date:  2002-06-14       Impact factor: 4.354

9.  A short and convenient chemical route to optically pure 2-methyl chromanmethanols. Total asymmetric synthesis of beta-, gamma-, and delta-tocotrienols.

Authors:  Elias A Couladouros; Vassilios I Moutsos; Maria Lampropoulou; James L Little; John A Hyatt
Journal:  J Org Chem       Date:  2007-08-09       Impact factor: 4.354

10.  Trans-hydrometalation of alkynes by a combination of InCl3 and DIBAL-H: one-pot access to functionalized (Z)-alkenes.

Authors:  Kazuaki Takami; Hideki Yorimitsu; Koichiro Oshima
Journal:  Org Lett       Date:  2002-08-22       Impact factor: 6.005
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