Kinetic Resolution of 2‐N‐Acylamido Tertiary Allylic Alcohols: Asymmetric Synthesis of Oxazolines

A series of cyclohexyl‐fused SPINOL‐derived phosphoric acids (Cy‐SPA) have been developed to catalyze the kinetic resolution of 2‐N‐acylamido tertiary allylic alcohols, providing access to chiral oxazolines bearing C‐2 alkyl substituents with high enantioselectivities (with s‐factors up to 153). Gra...

Full description

Saved in:
Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 363; no. 1; pp. 200 - 207
Main Authors Pan, Yongkai, Jiang, Qianwen, Rajkumar, Subramani, Zhu, Chaofan, Xie, Jinglei, Yu, Shaoze, Chen, Yunrong, He, Yu‐Peng, Yang, Xiaoyu
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 05.01.2021
Wiley Subscription Services, Inc
Subjects
Alcohols
Asymmetric catalysis
Chemistry
Chemistry, Applied
Chemistry, Organic
Kinetic resolution
Novel spirocyclic phosphoric acids
Organocatalysis
Oxazolines
Phosphoric acid
Physical Sciences
Science & Technology
BRONSTED ACID
Oxazolines
ALDOL REACTIONS
Asymmetric catalysis
Organocatalysis
PHOSPHORIC-ACIDS
ENANTIOSELECTIVE BROMOCYCLIZATION
Alcohols
DESYMMETRIZATION
KETONES
Novel spirocyclic phosphoric acids
CONSTRUCTION
Kinetic resolution
EFFICIENT
CATALYSTS
1,1'-SPIROBIINDANE-7,7'-DIOL
Online AccessGet full text

Cover

More Information
Summary:A series of cyclohexyl‐fused SPINOL‐derived phosphoric acids (Cy‐SPA) have been developed to catalyze the kinetic resolution of 2‐N‐acylamido tertiary allylic alcohols, providing access to chiral oxazolines bearing C‐2 alkyl substituents with high enantioselectivities (with s‐factors up to 153). Gram‐scale reaction with 1 mol% catalyst loading and transformations of the chiral products demonstrates the value of these methods.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202001051