Synlett 2020; 31(06): 523-534
DOI: 10.1055/s-0039-1690722
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© Georg Thieme Verlag Stuttgart · New York

Multiselective Catalytic Asymmetric Reactions Using α-Keto Esters as Pronucleophiles

a   RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan
b   RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan   Email: sohtome@riken.jp   Email: sodeoka@riken.jp
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a   RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan
b   RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan   Email: sohtome@riken.jp   Email: sodeoka@riken.jp
› Author Affiliations
This work was supported in part by RIKEN’s Strategic Programs and KAKENHI (Grant Numbers JP17H02213, 18K19156 and JP18H04277 in Precisely Designed Catalysts with Customized Scaffolding) from the Japan Society for the Promotion of Science (JSPS) and the Ministry of Education, Culture, Sports, Science and Technology (MEXT).
Further Information

Publication History

Received: 29 August 2019

Accepted after revision: 07 October 2019

Publication Date:
28 October 2019 (online)


In memory of Professor Dieter Enders

Published as part of the ISySyCat2019 Special Issue

Abstract

In the reactions of simple starting materials, precise catalytic control of the stereochemical outcome (enantio- and diastereoselectivity), as well as chemoselectivity and regioselectivity is an efficient approach to increase molecular complexity with minimal use of protecting groups. Here, we introduce our ongoing studies on asymmetric catalytic reactions using α-keto esters as pronucleophiles or formal 1,3-dipolarophiles. Capitalizing on the high tunability of our late transition-metal complexes with a suitable basic counteranion, we have established a range of multiselective catalytic protocols starting from α-keto esters to provide a wide variety of stereochemically complex molecules incorporating adjacent stereocenters.

1 Introduction

2 Catalytic Asymmetric Monofluorination with NSFI

3 Catalytic Asymmetric Michael Reaction with Nitroolefins

4 Catalytic Asymmetric [3+2] Cycloaddition with (E)-Nitrones

5 Catalytic Asymmetric [3+2] Cycloaddition with Nitrile Oxides

6 Summary

 
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