Literature DB >> 19778085

Synthesis of (+)-CP-99,994 via Pd(0)-catalyzed asymmetric allylic and homoallylic C-H Diamination of terminal olefin.

Renzhong Fu1, Baoguo Zhao, Yian Shi.   

Abstract

This paper describes an asymmetric synthesis of the potent substance P receptor antagonist (+)-CP-99,994 from 4-phenyl-1-butene via Pd(0)-catalyzed asymmetric allylic and homoallylic C-H diamination.

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Year:  2009        PMID： 19778085      PMCID： PMC2752905          DOI： 10.1021/jo9015584

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


  18 in total

1.  Enantio- and diastereoselective catalytic Mannich-type reaction of a glycine schiff base using a chiral two-center phase-transfer catalyst.

Authors:  Akihiro Okada; Tomoyuki Shibuguchi; Takashi Ohshima; Hyuma Masu; Kentaro Yamaguchi; Masakatsu Shibasaki
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-18       Impact factor: 15.336

2.  A facile Pd(0)-catalyzed regio- and stereoselective diamination of conjugated dienes and trienes.

Authors:  Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

3.  Lactams as prostanoid receptor ligands. Part 4: 2-Piperidones as selective EP4 receptor agonists.

Authors:  Todd R Elworthy; Emma R Brill; Christopher C Caires; Woongki Kim; Leang K Lach; Jahari Laurant Tracy; San-San Chiou
Journal:  Bioorg Med Chem Lett       Date:  2005-05-16       Impact factor: 2.823

4.  A novel and highly regioselective approach to 5-methoxy-6-substituted-3-sulfonyl-delta-enlactams from 5-methoxy-3-sulfonyl glutarimide: synthesis of cis-2-substituted-3-piperidinols.

Authors:  Min-Ruei Tsai; Bo-Fong Chen; Chih-Ching Cheng; Nein-Chen Chang
Journal:  J Org Chem       Date:  2005-03-04       Impact factor: 4.354

5.  Design, synthesis, and proposed active site binding analysis of monocyclic 2-azetidinone inhibitors of prostate specific antigen.

Authors:  R M Adlington; J E Baldwin; G W Becker; B Chen; L Cheng; S L Cooper; R B Hermann; T J Howe; W McCoull; A M McNulty; B L Neubauer; G J Pritchard
Journal:  J Med Chem       Date:  2001-05-10       Impact factor: 7.446

6.  A direct stereoselective approach to trans-2,3-disubstituted piperidines: application in the synthesis of 2-Epi-CP-99,994 and (+)-epilupinine.

Authors:  M'hamed Ahari; Amandine Perez; Christine Menant; Jean-Luc Vasse; Jan Szymoniak
Journal:  Org Lett       Date:  2008-05-14       Impact factor: 6.005

7.  Concise asymmetric synthesis of (+)-CP-99,994 and (+)-L-733,060 via efficient construction of homochiral syn-1,2-diamines and syn-1,2-amino alcohols.

Authors:  Run-Hua Liu; Kai Fang; Bing Wang; Ming-Hua Xu; Guo-Qiang Lin
Journal:  J Org Chem       Date:  2008-03-11       Impact factor: 4.354

8.  Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation.

Authors:  Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  J Am Chem Soc       Date:  2008-06-13       Impact factor: 15.419

9.  Sulfinimine-derived 2,3-diamino esters in the asymmetric synthesis of piperidine (2S,3S)-(+)-CP-99,994.

Authors:  Franklin A Davis; Yanfeng Zhang; Danyang Li
Journal:  Tetrahedron Lett       Date:  2007-10-29       Impact factor: 2.415

10.  Enantioselective synthesis of primary 1-(aryl)alkylamines by nucleophilic 1,2-addition of organolithium reagents to hydroxyoxime ethers and application to asymmetric synthesis of G-protein-coupled receptor ligands.

Authors:  Masakazu Atobe; Naoki Yamazaki; Chihiro Kibayashi
Journal:  J Org Chem       Date:  2004-08-20       Impact factor: 4.354
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  7 in total

1.  Modular synthesis of 1,2-diamine derivatives by palladium-catalyzed aerobic oxidative cyclization of allylic sulfamides.

Authors:  Richard I McDonald; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2010-07-26       Impact factor: 15.336

2.  Modular Synthesis of 1,2-Diamine Derivatives via Palladium-Catalyzed Aerobic Oxidative Cyclization of Allylic Sulfamides.

Authors:  Richard I McDonald; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2010-07-26       Impact factor: 15.336

3.  Cu(I)-catalyzed diamination of conjugated dienes. Complementary regioselectivity from two distinct mechanistic pathways involving Cu(II) and Cu(III) species.

Authors:  Baoguo Zhao; Xingao Peng; Yingguang Zhu; Thomas A Ramirez; Richard G Cornwall; Yian Shi
Journal:  J Am Chem Soc       Date:  2011-12-02       Impact factor: 15.419

Review 4.  Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.

Authors:  Richard I McDonald; Guosheng Liu; Shannon S Stahl
Journal:  Chem Rev       Date:  2011-03-23       Impact factor: 60.622

5.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

6.  Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines.

Authors:  Xinxin Shao; Kangnan Li; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2018-05-30       Impact factor: 15.419

7.  Catalytic diamination of olefins via N-N bond activation.

Authors:  Yingguang Zhu; Richard G Cornwall; Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  Acc Chem Res       Date:  2014-11-17       Impact factor: 22.384
  7 in total

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