Organometallic Enantiomeric Scaffolding: General Access to 2-Substituted Oxa- and Azabicyclo[3.2.1]octenes via a Brønsted Acid Catalyzed [5 + 2] Cycloaddition Reaction-Reference-Cited by-同舟云学术

Organometallic Enantiomeric Scaffolding: General Access to 2-Substituted Oxa- and Azabicyclo[3.2.1]octenes via a Brønsted Acid Catalyzed [5 + 2] Cycloaddition Reaction

Published:2008-05-15 Issue:23 Volume:130 Page:7449-7458
ISSN:0002-7863
Container-title:Journal of the American Chemical Society
language:en
Short-container-title:J. Am. Chem. Soc.

Author:

Garnier Ethel C.¹,Liebeskind Lanny S.¹

Affiliation:

1. Emory University, Department of Chemistry, 1515 Dickey Drive, Atlanta, Georgia 30322

Publisher

American Chemical Society (ACS)

Subject

Colloid and Surface Chemistry,Biochemistry,General Chemistry,Catalysis

Link

https://pubs.acs.org/doi/pdf/10.1021/ja800664v

Reference63 articles.

1. Organometallic enantiomeric scaffolds: (1) the metal/ligand auxiliary attached to the unsaturated ligand influences novel reactions, controls non-traditional selectivities, and provides a dominant regio- and stereocontrol element on the scaffold that allows the predictable introduction of new stereocenters atmultiple sites around the unsaturated ligand, (2) a single metal/ligand auxiliary controls the introduction of multiple stereocenters over multiple steps, and (3) the organometallic nature of the scaffolding enables the use of stereodivergent tactics for the introduction of ring substituents.

2. Practical, Scalable, High-Throughput Approaches to η3-Pyranyl and η3-Pyridinyl Organometallic Enantiomeric Scaffolds Using the Achmatowicz Reaction

3. Enantiocontrolled Synthesis of 2,6-Disubstituted Piperidines by Desymmetrization of meso-η-(3,4,5)-Dihydropyridinylmolybdenum Complexes. Application to the Total Synthesis of (−)-Dihydropinidine and (−)-Andrachcinidine

4. Enantiocontrolled Synthesis of 2,3,6-Trisubstituted Piperidines Using (η3-Dihydropyridinyl)molybdenum Complexes as Chiral Scaffolds. Total Synthesis of (−)-Indolizidine 209B

5. (η3-Pyranyl)TpMo(CO)2 Complexes as Chiral Scaffolds for the Enantiocontrolled Construction of 2,3,6-Trisubstituted Dihydropyrans (Tp = Trispyrazolylborate)

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