Synthesis of [(R)‐DTBM‐SEGPHOS]NiCl2for the Enantioselective Acetal Formation fromN‐Propanoyl‐1,3‐Thiazinane‐2‐Thione and Trimethyl Orthoformate

Author:

Kennington Stuart C. D.,Romea* Pedro,Urpí* Fèlix

Abstract

AbstractThis chapter describes the procedure for synthesis of [(R)‐DTBM‐SEGPHOS]NiCl2for the enantioselective acetal formation fromN‐Propanoyl1,3‐Thiazinane‐2‐thione and trimethyl orthoformate. It presents some of the important points to be considered, the conditions that need to be maintained, characterization data, and the reagents required, as well as the techniques used and the equipment setup that are vital to carrying out the process. The chapter also describes the hazards associated with working with chemicals and the ways to deal with these hazards. The procedures in Organic Syntheses are intended for use only by persons with proper training in experimental organic chemistry. The enantioselective and catalytic construction of carbon–carbon bonds from enolates has attracted much attention in recent years.

Publisher

Wiley

Reference13 articles.

1. Secció de Química Orgànica Departament de Química Inorgànica i Orgànica & Institut de Biomedicina de la Universitat de Barcelona (IBUB) Universitat de Barcelona 08028 Barcelona Catalonia Spain. Email:pedro.romea@ub.edu;felix.urpi@ub.edu. (ORCID (PR): 0000‐0002‐0259‐9155; ORCID (FU) 0000‐0003‐4289‐6506); Financial support from the Spanish Ministerio de Ciencia Innovación y Universidades (MCIU)/Agencia Estatal de Investigación (AEI)/Fondo Europeo de Desarrollo Regional (FEDER UE) (Grant No. PGC2018‐094311‐B‐I00) and the Generalitat de Catalunya (2017SGR 271) as well as a doctorate studentship to S. C. D. K. (FI Generalitat de Catalunya) are acknowledged.

2. Ni(II) Bis(oxazoline)-Catalyzed Enantioselective Syn Aldol Reactions of N-Propionylthiazolidinethiones in the Presence of Silyl Triflates

3. Ni(II) Tol-BINAP-Catalyzed Enantioselective Orthoester Alkylations of N-Acylthiazolidinethiones

4. A Designed Amide as an Aldol Donor in the Direct Catalytic Asymmetric Aldol Reaction

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