Literature DB >> 15704912

Palladium/BINAP(S)-catalyzed asymmetric allylic amination.

J W Faller1, Jeremy C Wilt.   

Abstract

The enantioselective allylic amination of acyclic allylic carbonates catalyzed by a palladium/(S)-BINAP(S) system was investigated. Amination of several substrates proceeded with high ee. Crotyl carbonates show an unusually high regioselectivity for the branched isomer. The use of (S)-TolBINAP(S) and (S)-3,5-xylyl-BINAP(S) as ligands was found to increase the enantioselectivity of the aminations. A P,S binding mode of the BINAP(S) ligand was found in an X-ray crystallographic study. [reaction: see text]

Entities:  

Year:  2005        PMID： 15704912     DOI： 10.1021/ol047624k

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


  3 in total

1.  Primary tert- and sec-allylamines via palladium-catalyzed hydroamination and allylic substitution with hydrazine and hydroxylamine derivatives.

Authors:  Adam M Johns; Zhijian Liu; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Asymmetric synthesis of α-alkenyl homoallylic primary amines via 1,2-addition of Grignard reagent to α,β-unsaturated phosphonyl imines.

Authors:  Yiwen Xiong; Haibo Mei; Chen Xie; Jianlin Han; Guigen Li; Yi Pan
Journal:  RSC Adv       Date:  2013-01-01       Impact factor: 3.361

3.  Exercising regiocontrol in palladium-catalyzed asymmetric prenylations and geranylation: unifying strategy toward flustramines A and B.

Authors:  Barry M Trost; Sushant Malhotra; Walter H Chan
Journal:  J Am Chem Soc       Date:  2011-04-26       Impact factor: 15.419
  3 in total

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