Literature DB >> 15179475

Allylation and highly diastereoselective syn or anti crotylation of N-toluenesulfonylimines using potassium allyl- and crotyltrifluoroborates.

Sze-Wan Li1, Robert A Batey.   

Abstract

Air and moisture stable potassium allyl- and crotyltrifluoroborates undergo addition to N-sulfonyl and N-sulfinyl aldimines in the presence of Lewis acids, to provide the corresponding homoallylic amines in high yields and excellent diastereoselectivity.

Entities:  

Year:  2004        PMID： 15179475     DOI： 10.1039/b403759f

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  7 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.  Synthesis of functionalized organotrifluoroborates via the 1,3-dipolar cycloaddition of azides.

Authors:  Gary A Molander; Jungyeob Ham
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

3.  Linchpin synthons: metalation of aryl bromides bearing a potassium trifluoroborate moiety.

Authors:  Gary A Molander; Noel M Ellis
Journal:  J Org Chem       Date:  2006-09-15       Impact factor: 4.354

4.  cis-dihydroxylation of unsaturated potassium alkyl- and aryltrifluoroborates.

Authors:  Gary A Molander; Ruth Figueroa
Journal:  Org Lett       Date:  2006-01-05       Impact factor: 6.005

5.  Functionalization of organotrifluoroborates: reductive amination.

Authors:  Gary A Molander; David J Cooper
Journal:  J Org Chem       Date:  2008-04-16       Impact factor: 4.354

6.  Complex allylation by the direct cross-coupling of imines with unactivated allylic alcohols.

Authors:  Masayuki Takahashi; Martin McLaughlin; Glenn C Micalizio
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

7.  Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization.

Authors:  Rubén M Carballo; José M Padrón; Israel Fernández; Daniel A Cruz; Luana Grmuša; Víctor S Martín; Juan I Padrón
Journal:  J Org Chem       Date:  2022-08-03       Impact factor: 4.198
  7 in total

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