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Literature DB >> 19053421

Conversion of allylic alcohols to stereodefined trisubstituted alkenes: a complementary process to the Claisen rearrangement.

Abstract

A stereoselective method for the conversion of allylic alcohols to (Z)-trisubstituted alkenes is presented. Overall, the reaction sequence described is stereochemically complementary to related Claisen rearrangement reactions--processes that typically deliver the stereoisomeric trisubstituted alkene containing products.

Entities: Chemical

Mesh：

Substances：

Year: 2008 PMID： 19053421 PMCID： PMC2732435 DOI： 10.1021/ja8074242

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

5 in total

1. Synthesis of substituted 1,4-dienes by direct alkylation of allylic alcohols.

Authors: Filip Kolundzic; Glenn C Micalizio
Journal: J Am Chem Soc Date: 2007-11-16 Impact factor: 15.419

2. Generation of a silylethylene-titanium alkoxide complex. A versatile reagent for silylethylation and silylethylidenation of unsaturated compounds

Authors:
Journal: J Org Chem Date: 2000-09-22 Impact factor: 4.354

3. 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

4. Allene-alkyne cross-coupling for stereoselective synthesis of substituted 1,4-dienes and cross-conjugated trienes.

Authors: Heidi L Shimp; Alissa Hare; Martin McLaughlin; Glenn C Micalizio
Journal: Tetrahedron Date: 2008-04-14 Impact factor: 2.457

5. Sulfinyl-mediated chirality transfer in diastereoselective Claisen rearrangements.

Authors: Roberto Fernández de la Pradilla; Carlos Montero; Mariola Tortosa
Journal: Org Lett Date: 2002-07-11 Impact factor: 6.005

5 in total

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. Reaction design, discovery, and development as a foundation to function-oriented synthesis.

Authors: Glenn C Micalizio; Sarah B Hale
Journal: Acc Chem Res Date: 2015-02-10 Impact factor: 22.384

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. Generation of quaternary centers by reductive cross-coupling: shifting of regioselectivity in a subset of allylic alcohol-based coupling reactions.

Authors: Dexi Yang; Justin K Belardi; Glenn C Micalizio
Journal: Tetrahedron Lett Date: 2011-04-27 Impact factor: 2.415

10. The regio- and stereochemical course of reductive cross-coupling reactions between 1,3-disubstituted allenes and vinylsilanes: Synthesis of (Z)-dienes.

Authors: Allan U Barlan; Glenn C Micalizio
Journal: Tetrahedron Date: 2010-06-26 Impact factor: 2.457

Conversion of allylic alcohols to stereodefined trisubstituted alkenes: a complementary process to the Claisen rearrangement.

1. Synthesis of substituted 1,4-dienes by direct alkylation of allylic alcohols.

2. Generation of a silylethylene-titanium alkoxide complex. A versatile reagent for silylethylation and silylethylidenation of unsaturated compounds

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

4. Allene-alkyne cross-coupling for stereoselective synthesis of substituted 1,4-dienes and cross-conjugated trienes.

5. Sulfinyl-mediated chirality transfer in diastereoselective Claisen rearrangements.

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

2. Reaction design, discovery, and development as a foundation to function-oriented synthesis.

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

4. Generation of quaternary centers by reductive cross-coupling: shifting of regioselectivity in a subset of allylic alcohol-based coupling reactions.

5. Alkenenitrile Transmissive Olefination: Synthesis of the Putative Lignan "Morinol I"

6. Convergent synthesis of deoxypropionates.

7. Metallacycle-Mediated Cross-Coupling with Substituted and Electronically Unactivated Alkenes.

8. Convergent synthesis of stereodefined exo-alkylidene-gamma-lactams from beta-halo allylic alcohols.

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

10. The regio- and stereochemical course of reductive cross-coupling reactions between 1,3-disubstituted allenes and vinylsilanes: Synthesis of (Z)-dienes.