Recent Advances in the Synthesis of Enantiomerically Enriched Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols through Addition of Organometallic Reagents to Carbonyl Compounds

Wystan K. O. Teixeira; Danilo Yano de Albuquerque; Senthil Narayanaperumal; Ricardo S. Schwab

doi:10.1055/s-0039-1690847

Synthesis, Table of Contents

Synthesis 2020; 52(13): 1855-1873
DOI: 10.1055/s-0039-1690847

review

Recent Advances in the Synthesis of Enantiomerically Enriched Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols through Addition of Organometallic Reagents to Carbonyl Compounds

Wystan K. O. Teixeira

^aCentre of Excellence for Research in Sustainable Chemistry (CERSusChem), Departamento de Química, Universidade Federal de São Carlos – UFSCar, Rodovia Washington Luís, km 235 - SP-310, São Carlos, São Paulo 13565-905, Brazil Email: rschwab@ufscar.br

,

Danilo Yano de Albuquerque

^aCentre of Excellence for Research in Sustainable Chemistry (CERSusChem), Departamento de Química, Universidade Federal de São Carlos – UFSCar, Rodovia Washington Luís, km 235 - SP-310, São Carlos, São Paulo 13565-905, Brazil Email: rschwab@ufscar.br

,

Senthil Narayanaperumal∗

^bHead-Department of Chemistry, Dayananda Sagar Academy of Technology & Management-DSATM, Kanakapura Road, Bengaluru-560082, India Email: senthilnp@yahoo.com

,

Ricardo S. Schwab ∗

^aCentre of Excellence for Research in Sustainable Chemistry (CERSusChem), Departamento de Química, Universidade Federal de São Carlos – UFSCar, Rodovia Washington Luís, km 235 - SP-310, São Carlos, São Paulo 13565-905, Brazil Email: rschwab@ufscar.br

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Abstract

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Abstract

Enantiomerically enriched diaryl, aryl heteroaryl, and diheteroaryl alcohols are an important family of compounds known for their biological properties. Moreover, these molecules are highly privileged scaffolds used as building blocks for the synthesis of pharmaceutically relevant products. This short review provides background on the enantioselective arylation and heteroarylation of carbonyl compounds, as well as, the most significant improvements in this field with special emphasis on the application of organometallic reagents.

1 Introduction

2 Background on the Enantioselective Synthesis of Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols

3 Organozinc Reagents

4 Organolithium Reagents

5 Grignard Reagents

6 Organoaluminum Reagents

7 Organotitanium Reagents

8 Organobismuth Reagents

9 Miscellaneous

10 Conclusion

Key words

chiral alcohols - organometallic reagents - asymmetric addition - enantioselective arylation - heteroarylation

Full Text

References

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