Synthesis 2020; 52(13): 1855-1873
DOI: 10.1055/s-0039-1690847
review
© Georg Thieme Verlag Stuttgart · New York

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
a   Centre 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
a   Centre 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
b   Head-Department of Chemistry, Dayananda Sagar Academy of Technology & Management-DSATM, Kanakapura Road, Bengaluru-560082, India   Email: senthilnp@yahoo.com
,
a   Centre 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
› Author Affiliations
The authors are grateful to the funding agencies that supported this work, Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP, 2013/06558-3 and 2014/50249-8), GlaxoSmithKline, Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq, 475203/2013-5) and Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES, 001) for financial support and fellowships.
Further Information

Publication History

Received: 13 December 2019

Accepted after revision: 08 February 2020

Publication Date:
16 March 2020 (online)


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