Literature DB >> 12790550

Asymmetric synthesis of allyl- and alpha-allenylamines from chiral imines and alkynes via (eta(2)-imine)Ti(O-i-Pr)2 complexes.

Kohki Fukuhara1, Sentaro Okamoto, Fumie Sato.   

Abstract

[reaction: see text] The reaction of a divalent titanium reagent Ti(O-i-Pr)(4)/2i-PrMgX with optically active arylaldimines derived from arylaldehydes and O-methylphenylglycinol provided, in a highly diastereoselective manner, chiral (eta(2)-imine)Ti(O-i-Pr)(2) complexes, which in turn reacted with 1-alkynes or propargyl compounds to give optically active allyl- and alpha-allenylamines, respectively.

Entities:  

Year:  2003        PMID： 12790550     DOI： 10.1021/ol034599u

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


  10 in total

1.  Preparation of stereodefined homoallylic amines from the reductive cross-coupling of allylic alcohols with imines.

Authors:  Ming Z Chen; Martin McLaughlin; Masayuki Takahashi; Michael A Tarselli; Dexi Yang; Shuhei Umemura; Glenn C Micalizio
Journal:  J Org Chem       Date:  2010-11-11       Impact factor: 4.354

2.  Regio- and stereoselective cross-coupling of substituted olefins and imines. A convergent stereoselective synthesis of saturated 1,5-amino-alcohols and substituted piperidines.

Authors:  Masayuki Takahashi; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2007-05-26       Impact factor: 15.419

3.  Regioselective Reductive Cross-Coupling Reactions of Unsymmetrical Alkynes.

Authors:  Holly A Reichard; Martin McLaughlin; Ming Z Chen; Glenn C Micalizio
Journal:  European J Org Chem       Date:  2010-01

4.  Regio- and Stereoselective Direct Cross-Coupling of Aromatic Imines with Allenic Alcohols.

Authors:  Martin McLaughlin; Heidi L Shimp; Raul Navarro; Glenn C Micalizio
Journal:  Synlett       Date:  2008-03-01       Impact factor: 2.454

5.  Convergent synthesis of piperidines by the union of conjugated alkynes with imines: a unique regioselective bond construction for heterocycle synthesis.

Authors:  Ming Z Chen; Glenn C Micalizio
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

6.  Aliphatic imines in titanium-mediated reductive cross-coupling: unique reactivity of Ti(O-i-Pr)4/n-BuLi.

Authors:  Michael A Tarselli; Glenn C Micalizio
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

7.  An alkoxide-directed intermolecular [2+2+1] annulation: a three-component coupling reaction for the synthesis of tetrasubstituted alpha,beta-unsaturated gamma-lactams.

Authors:  Martin McLaughlin; Masayuki Takahashi; Glenn C Micalizio
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

8.  Niobium- and zirconium-catalyzed reactions of substituted 2 alkynylamines with Et2Zn.

Authors:  Rita N Kadikova; Ilfir R Ramazanov; Azat M Gabdullin; Oleg S Mozgovoj; Usein M Dzhemilev
Journal:  RSC Adv       Date:  2021-01-22       Impact factor: 3.361

9.  Titanium-mediated reductive cross-coupling reactions of imines with terminal alkynes: An efficient route for the synthesis of stereodefined allylic amines.

Authors:  Kebin Mao; Guoqin Fan; Yuanhong Liu; Shi Li; Xu You; Dan Liu
Journal:  Beilstein J Org Chem       Date:  2013-03-27       Impact factor: 2.883

10.  An annulation reaction for the synthesis of cross-conjugated triene-containing hydroindanes from acyclic precursors.

Authors:  Xiayun Cheng; Glenn C Micalizio
Journal:  Org Lett       Date:  2014-09-12       Impact factor: 6.005
  10 in total

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