Literature DB >> 22738671

Divergent stereocontrol of acid catalyzed intramolecular aldol reactions of 2,3,7-triketoesters: synthesis of highly functionalized cyclopentanones.

Phong Truong1, Charles S Shanahan, Michael P Doyle.   

Abstract

The intramolecular acid catalyzed aldol cyclization of 2,3,7-triketoesters formed from ζ-keto-α-diazo-β-ketoesters provides highly functionalized cyclopentanones with good diastereoselectivity in high overall yields via kinetically controlled and stereodivergent catalytic processes. Lewis acid catalysis gives high selectivity for the 1,2-anti tetrasubstituted cyclopentanones, whereas Brønsted acid catalysis produces the corresponding 1,2-syn diastereomer.

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Year:  2012        PMID： 22738671      PMCID： PMC3480983          DOI： 10.1021/ol301317a

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


  26 in total

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4.  Synthesis of cyclopentitols by ring-closing approaches.

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5.  Total synthesis of (+)-przewalskin B.

Authors:  Xiaotao Zhuo; Kai Xiang; Fu-Min Zhang; Yong-Qiang Tu
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6.  Multifunctionalized 3-hydroxypyrroles in a three-step, one-pot cascade process from methyl 3-TBSO-2-diazo-3-butenoate and nitrones.

Authors:  Xinfang Xu; Maxim O Ratnikov; Peter Y Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2011-10-27       Impact factor: 6.005

7.  Theoretical study of intramolecular aldol condensation of 1, 6-diketones: trimethylsilyl substituent effect

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Journal:  J Org Chem       Date:  2000-09-08       Impact factor: 4.354

8.  Development of novel Lewis acid catalysts for selective organic reactions in aqueous media.

Authors:  Shu Kobayashi; Kei Manabe
Journal:  Acc Chem Res       Date:  2002-04       Impact factor: 22.384

9.  Ni(II) bis(oxazoline)-catalyzed enantioselective syn aldol reactions of N-propionylthiazolidinethiones in the presence of silyl triflates.

Authors:  David A Evans; C Wade Downey; Jed L Hubbs
Journal:  J Am Chem Soc       Date:  2003-07-23       Impact factor: 15.419

10.  Catalytic asymmetric hydroxymethylation of silicon enolates using an aqueous solution of formaldehyde with a chiral scandium complex.

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Journal:  J Am Chem Soc       Date:  2004-10-06       Impact factor: 15.419
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  7 in total

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Authors:  Rebecca B Watson; Corinna S Schindler
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Review 2.  Cycloaddition reactions of enoldiazo compounds.

Authors:  Qing-Qing Cheng; Yongming Deng; Marianne Lankelma; Michael P Doyle
Journal:  Chem Soc Rev       Date:  2017-08-29       Impact factor: 54.564

3.  Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement.

Authors:  Qiang Sha; Hadi Arman; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2016-01-04       Impact factor: 6.222

4.  Direct access to 6/5/7/5- and 6/7/5/5-fused tetracyclic triterpenoids via divergent transannular aldol reaction of lanosterol-derived diketone.

Authors:  Vasily A Ignatenko; Yong Han; Gregory P Tochtrop
Journal:  J Org Chem       Date:  2013-11-12       Impact factor: 4.354

5.  Functionalizing the γ-Position of α-Diazo-β-ketoesters.

Authors:  Thu Q Nguyen; Maha Alqurafi; Cash Edwards; Pauline Nguyen; Jean Kim; Samuel Casco; Maricka Bennet; Christopher Chiang; Maureen Lohry; Melina Cox; Byron Meshram; Duyen Le; Eugene Kim; Snigdha Smriti; Peter Oelschlaeger; John D Buynak
Journal:  Tetrahedron Lett       Date:  2016-06-16       Impact factor: 2.415

6.  [3+2] Cycloaddition of alkyl aldehydes and alkynes enabled by photoinduced hydrogen atom transfer.

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Review 7.  Vicinal ketoesters - key intermediates in the total synthesis of natural products.

Authors:  Marc Paul Beller; Ulrich Koert
Journal:  Beilstein J Org Chem       Date:  2022-09-15       Impact factor: 2.544
  7 in total

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