Literature DB >> 18351770

Construction of highly functionalized diazoacetoacetates via catalytic Mukaiyama-Michael reactions.

Yu Liu1, Yu Zhang, Noel Jee, Michael P Doyle.   

Abstract

Functionalized diazo acetoacetates are prepared by an efficient Mukaiyama-Michael reaction between methyl 3-(trialkylsilanoxy)-2-diazo-3-butenoate and alpha,beta-unsaturated enones. Vinyl ether and ketone derivatives are both accessible in good to excellent yield through this methodology. The mild Lewis acid zinc(II) triflate is the optimal catalyst, and its loading can be as low as 0.1 mol %. In addition, zinc triflate was also found to be a superior catalyst for the related Mukaiyama-aldol reaction.

Entities:  

Mesh：

Substances：

Year:  2008        PMID： 18351770      PMCID： PMC3119889          DOI： 10.1021/ol800298n

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


  12 in total

1.  Recent Advances in Asymmetric Catalytic Metal Carbene Transformations.

Authors:  Michael P. Doyle; David C. Forbes
Journal:  Chem Rev       Date:  1998-04-02       Impact factor: 60.622

2.  Asymmetric Michael addition reactions of 2-silyloxyfurans catalyzed by binaphthyldiimine-Ni(II) complexes.

Authors:  Hiroyuki Suga; Takeo Kitamura; Akikazu Kakehi; Toshihide Baba
Journal:  Chem Commun (Camb)       Date:  2004-05-17       Impact factor: 6.222

3.  Asymmetric conjugate addition of silyl enol ethers catalyzed by tethered Bis(8-quinolinolato) aluminum complexes.

Authors:  Norito Takenaka; Joshua P Abell; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

4.  Design of a small-molecule catalyst using intramolecular cation-pi interactions for enantioselective Diels-Alder and Mukaiyama-Michael reactions: L-DOPA-derived monopeptide.Cu(II) complex.

Authors:  Kazuaki Ishihara; Makoto Fushimi
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

5.  Organotin perfluorooctanesulfonates as air-stable Lewis acid catalysts: synthesis, characterization, and catalysis.

Authors:  De Lie An; Zhihong Peng; Akihiro Orita; Akinobu Kurita; Sumiyo Man-e; Kei Ohkubo; Xingshu Li; Shunichi Fukuzumi; Junzo Otera
Journal:  Chemistry       Date:  2006-02-08       Impact factor: 5.236

6.  Enantioselective and diastereoselective Mukaiyama-Michael reactions catalyzed by bis(oxazoline) copper(II) complexes.

Authors:  D A Evans; K A Scheidt; J N Johnston; M C Willis
Journal:  J Am Chem Soc       Date:  2001-05-16       Impact factor: 15.419

7.  Dimethylsilyl ketene acetal as a nucleophile in asymmetric Michael reaction: enhanced enantioselectivity in oxazaborolidinone-catalyzed reaction.

Authors:  Toshiro Harada; Shinya Adachi; Xiaowei Wang
Journal:  Org Lett       Date:  2004-12-23       Impact factor: 6.005

8.  Highly Selective 1,2- and 1,4-Addition of Silyl Enol Ethers to alpha,beta-Unsaturated Carbonyl Compounds in 5 M Lithium Perchlorate-Nitromethane Medium.

Authors:  S. Sankararaman; R. Sudha
Journal:  J Org Chem       Date:  1999-03-19       Impact factor: 4.354

9.  Catalytic addition methods for the synthesis of functionalized diazoacetoacetates and application to the construction of highly substituted cyclobutanones.

Authors:  Michael P Doyle; Kousik Kundu; Albert E Russell
Journal:  Org Lett       Date:  2005-11-10       Impact factor: 6.005

10.  Enantioselective Lewis acid-catalyzed Mukaiyama-Michael reactions of acyclic enones. Catalysis by allo-threonine-derived oxazaborolidinones.

Authors:  Xiaowei Wang; Shinya Adachi; Hiroyoshi Iwai; Hiroshi Takatsuki; Katsuhiro Fujita; Mikako Kubo; Akira Oku; Toshiro Harada
Journal:  J Org Chem       Date:  2003-12-26       Impact factor: 4.354
View more
  9 in total

1.  Highly enantioselective catalytic synthesis of functionalized chiral diazoacetoacetates.

Authors:  Xinfang Xu; Wen-Hao Hu; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-31       Impact factor: 15.336

2.  Competitive [2,3]- and [1,2]-oxonium ylide rearrangements. Concerted or stepwise?

Authors:  Deana M Jaber; Ryan N Burgin; Matthew Helper; Peter Y Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2012-03-12       Impact factor: 6.005

Review 3.  Diazo Compounds: Versatile Tools for Chemical Biology.

Authors:  Kalie A Mix; Matthew R Aronoff; Ronald T Raines
Journal:  ACS Chem Biol       Date:  2016-10-26       Impact factor: 5.100

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

Authors:  Phong Truong; Charles S Shanahan; Michael P Doyle
Journal:  Org Lett       Date:  2012-06-28       Impact factor: 6.005

5.  Diazoacetoacetate enones for the synthesis of diverse natural product-like scaffolds.

Authors:  Charles S Shanahan; Phong Truong; Savannah M Mason; John S Leszczynski; Michael P Doyle
Journal:  Org Lett       Date:  2013-07-05       Impact factor: 6.005

6.  Pericyclic reaction of a zwitterionic salt of an enedione-diazoester. A novel strategy for the synthesis of highly functionalized resorcinols.

Authors:  Yu Liu; Kanwarpal Bakshi; Peter Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2010-10-01       Impact factor: 6.005

7.  A phosphine-mediated conversion of azides into diazo compounds.

Authors:  Eddie L Myers; Ronald T Raines
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  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

9.  Stereoselective synthesis of highly functionalized alpha-diazo-beta-ketoalkanoates via catalytic one-pot Mukaiyama-Aldol reactions.

Authors:  Lei Zhou; Michael P Doyle
Journal:  Org Lett       Date:  2010-02-19       Impact factor: 6.005
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.