Literature DB >> 20932043

Domino imino-aldol-aza-Michael reaction: one-pot diastereo- and enantioselective synthesis of piperidines.

Manas K Ghorai1, Sandipan Halder, Raj Kumar Das.   

Abstract

Addition of α-arylmethylidene- or α-alkylidene-β-keto ester enolate to N-activated aldimines via the imino aldol pathway followed by intramolecular aza-Michael reaction in a domino fashion has been developed, and a highly diastereoselective route to substituted piperidines is reported. Enantiopure piperidines are synthesized from chiral sulfinyl imines. Formation and the observed stereoselectivity of the products have been rationalized by mechanistic and computational studies.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20932043     DOI： 10.1021/jo101680f

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


  7 in total

1.  Synthesis of a Library of 1,5,2-Dithiazepine 1,1-Dioxides. Part 1: A One-Pot Sulfonylation/Thia-Michael Protocol.

Authors:  Qin Zang; Aihua Zhou; Salim Javed; Pradip K Maity; Chris A Knudtson; Danse Bi; Jared J Hastings; Fatima Z Basha; Paul R Hanson
Journal:  Heterocycles       Date:  2012-12-31       Impact factor: 0.831

Review 2.  Transition metal-free one-pot synthesis of nitrogen-containing heterocycles.

Authors:  Simpal Kumari; Dharma Kishore; Sarvesh Paliwal; Rajani Chauhan; Jaya Dwivedi; Aakanksha Mishra
Journal:  Mol Divers       Date:  2015-06-09       Impact factor: 2.943

3.  Triazole-containing isothiazolidine 1,1-dioxide library synthesis: one-pot, multi-component protocols for small molecular probe discovery.

Authors:  Alan Rolfe; Thomas O Painter; Naeem Asad; Moon Young Hur; Kyu Ok Jeon; Marek Brzozowski; Sarra V Klimberg; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Conrad Santini; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2011-08-25       Impact factor: 3.784

4.  Application of a Double Aza-Michael Reaction in a 'Click, Click, Cy-Click' Strategy: From Bench to Flow.

Authors:  Qin Zang; Salim Javed; Farman Ullah; Aihua Zhou; Christopher A Knudtson; Danse Bi; Fatima Z Basha; Michael G Organ; Paul R Hanson
Journal:  Synthesis (Stuttg)       Date:  2011-09-01       Impact factor: 3.157

5.  Highly diastereoselective synthesis of tetrahydropyridines by a C-H activation-cyclization-reduction cascade.

Authors:  Simon Duttwyler; Colin Lu; Arnold L Rheingold; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2012-02-22       Impact factor: 15.419

6.  Condensation reactions of guanidines with bis-electrophiles: Formation of highly nitrogenous heterocycles.

Authors:  David M Arnold; Matthew G Laporte; Shelby M Anderson; Peter Wipf
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

7.  Synthesis, spectroscopic characterization, X-ray structure, and DFT calculations of some new 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxamides.

Authors:  Yi Li; Yuan-Yuan Liu; Xue-Jun Chen; Xiao-Hui Xiong; Fang-Shi Li
Journal:  PLoS One       Date:  2014-03-13       Impact factor: 3.240
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.