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Literature DB >> 12904019

Toward a versatile allylation reagent: practical, enantioselective allylation of acylhydrazones using strained silacycles.

Richard Berger¹, Philippe M A Rabbat, James L Leighton.

Abstract

A highly practical method for the enantioselective allylation of acylhydrazones has been developed. The previously reported strained silacycle reagent 1 reacts with a wide variety of acylhydrazones to give the hydrazide products with good enantioselectivity (83-89% ee, typically). It has been demonstrated that the products may be isolated without chromatography by recrystallization in >/=98% ee.

Entities: Chemical

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Year: 2003 PMID： 12904019 DOI： 10.1021/ja035001g

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

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Cited

11 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. Delayed catalyst function enables direct enantioselective conversion of nitriles to NH₂-amines.

Authors: Shaochen Zhang; Juan Del Pozo; Filippo Romiti; Yucheng Mu; Sebastian Torker; Amir H Hoveyda
Journal: Science Date: 2019-04-05 Impact factor: 47.728

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

4. Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective γ-Additions of Allylboron Moieties to Aldimines.

Authors: Farid W van der Mei; Hiroshi Miyamoto; Daniel L Silverio; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2016-03-09 Impact factor: 15.336

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

Authors: Yao Jiang; Scott E Schaus
Journal: Angew Chem Int Ed Engl Date: 2017-01-04 Impact factor: 15.336

6. Synthesis of enantioenriched homopropargylic sulfonamides by a three component reaction of aldehydes, sulfonamides, and chiral allenylsilanes.

Authors: Ryan A Brawn; James S Panek
Journal: Org Lett Date: 2009-10-01 Impact factor: 6.005

Toward a versatile allylation reagent: practical, enantioselective allylation of acylhydrazones using strained silacycles.

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

2. Delayed catalyst function enables direct enantioselective conversion of nitriles to NH₂-amines.

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. Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective γ-Additions of Allylboron Moieties to Aldimines.

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

6. Synthesis of enantioenriched homopropargylic sulfonamides by a three component reaction of aldehydes, sulfonamides, and chiral allenylsilanes.

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

8. Strategies and Methods for the Synthesis of Anticancer Natural Product Neopeltolide and its Analogs.

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

10. Stereoselective cross-coupling between allylic alcohols and aldimines.