Literature DB >> 20377201

Asymmetric, organocatalytic, three-step synthesis of alpha-hydroxy-(E)-beta,gamma-unsaturated esters.

Lindsey C Hess1, Gary H Posner.   

Abstract

An efficient and enantiocontrolled three-step synthesis of alpha-hydroxy-(E)-beta,gamma-unsaturated esters is reported. Enantioenriched alpha-selenyl aldehydes, prepared in one step by asymmetric, organocatalytic alpha-selenylation of aldehydes, were directly subjected to a Wittig reaction followed by allylic selenide to selenoxide oxidation and final spontaneous [2,3]-sigmatropic rearrangement to yield the target compounds in 43-65% overall yield and in 94-97% ee.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20377201      PMCID： PMC2864524          DOI： 10.1021/ol100615j

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


  8 in total

1.  Synthesis of a cytotoxic vernolepin prototype. Ozonization of silyloxyalkenes.

Authors:  R D Clark; C H Heathcock
Journal:  J Org Chem       Date:  1976-04-16       Impact factor: 4.354

2.  Organocatalytic asymmetric alpha-selenenylation of aldehydes.

Authors:  Marcello Tiecco; Armando Carlone; Silvia Sternativo; Francesca Marini; Giuseppe Bartoli; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Application of the claisen rearrangement to the synthesis of trans trisubstituted olefinic bonds. Synthesis of squalene and insect juvenile hormone.

Authors:  D J Faulkner; M R Petersen
Journal:  J Am Chem Soc       Date:  1973-01-24       Impact factor: 15.419

4.  Total syntheses of symbioramide derivatives from l-serine and their antileukemic activities.

Authors:  Hideki Azuma; Ryoko Takao; Hayato Niiro; Keiji Shikata; Seizo Tamagaki; Taro Tachibana; Kenji Ogino
Journal:  J Org Chem       Date:  2003-04-04       Impact factor: 4.354

5.  Antiproliferative Hybrid Analogs of the Hormone 1alpha,25-Dihydroxyvitamin D(3): Design, Synthesis, and Preliminary Biological Evaluation.

Authors:  Gary H. Posner; Jae Kyoo Lee; M. Christina White; Richard H. Hutchings; Haiyan Dai; Joseph L. Kachinski; Patrick Dolan; Thomas W. Kensler
Journal:  J Org Chem       Date:  1997-05-16       Impact factor: 4.354

6.  Asymmetric, organocatalytic, three-step synthesis of gamma-hydroxy-(E)-alpha,beta-unsaturated sulfones and esters.

Authors:  Kimberly S Petersen; Gary H Posner
Journal:  Org Lett       Date:  2008-09-24       Impact factor: 6.005

7.  Enantioselective reductive coupling of 1,3-enynes to glyoxalates mediated by hydrogen: asymmetric synthesis of beta,gamma-unsaturated alpha-hydroxy esters.

Authors:  Young-Taek Hong; Chang-Woo Cho; Eduardas Skucas; Michael J Krische
Journal:  Org Lett       Date:  2007-08-18       Impact factor: 6.005

8.  Studies toward the enantioselective syntheses of oxylipins: total synthesis and structure revision of solandelactone E.

Authors:  Jennifer E Davoren; Christian Harcken; Stephen F Martin
Journal:  J Org Chem       Date:  2007-12-19       Impact factor: 4.354
  8 in total
  1 in total

1.  Three-component, one-flask synthesis of rhodanines (thiazolidinones).

Authors:  Alexander M Jacobine; Gary H Posner
Journal:  J Org Chem       Date:  2011-08-31       Impact factor: 4.354
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.