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Literature DB >> 16866515

Asymmetric allylboration of cyclic imines and applications to alkaloid synthesis.

Abstract

Treatment of cyclic imines with 3,3'-disubstituted binaphthol modified allylboronates provides the expected allylated products in good yields and with high stereoselectivities (91-99% ee). The products may be readily transformed into various alkaloids.

Entities: Chemical

Year: 2006 PMID： 16866515 DOI： 10.1021/ja0636791

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

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. Ni- and Pd-catalyzed synthesis of substituted and functionalized allylic boronates.

Authors: Ping Zhang; Ian A Roundtree; James P Morken
Journal: Org Lett Date: 2012-02-29 Impact factor: 6.005

3. Enantioselective synthesis of homoallylic amines through reactions of (pinacolato)allylborons with aryl-, heteroaryl-, alkyl-, or alkene-substituted aldimines catalyzed by chiral C1-symmetric NHC-Cu complexes.

Authors: Erika M Vieira; Marc L Snapper; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2011-02-22 Impact factor: 15.419

7. Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters.

Authors: Rauful Alam; Colin Diner; Sybrand Jonker; Lars Eriksson; Kálmán J Szabó
Journal: Angew Chem Int Ed Engl Date: 2016-10-13 Impact factor: 15.336

7 in total

Asymmetric allylboration of cyclic imines and applications to alkaloid synthesis.

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

2. Ni- and Pd-catalyzed synthesis of substituted and functionalized allylic boronates.

3. Enantioselective synthesis of homoallylic amines through reactions of (pinacolato)allylborons with aryl-, heteroaryl-, alkyl-, or alkene-substituted aldimines catalyzed by chiral C1-symmetric NHC-Cu complexes.

4. Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols.

5. Asymmetric allylboration of acyl imines catalyzed by chiral diols.

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

7. Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters.