Accessing chiral 2, 2-disubstituted morpholines via organocatalytic enantioselective chlorocycloetherification. Issue 16 (6th July 2022)

• Record Type: Journal Article
• Authors: Zhong, Haijing; Ding, Tengbo; Guo, Qifeng; Tian, Zeng; Yu, Pei; Jiang, Xiaojian
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 16(2022)
• Page Start: 4372
• Page End: 4378
• Publication Date: 2022-07-06
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo00390b
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A catalytic asymmetric halocycloetherification process is developed to achieve enantioenriched quaternary 2, 2-disubstituted morpholines using an organo-catalyst. Abstract : Chiral morpholine is an important scaffold in organic synthesis and a pharmacophore in medicinal chemistry. However, catalytic enantioselective procedures for the construction of morpholines remain sparse. We report herein a catalytic asymmetric halocyclization protocol to furnish morpholines containing a quaternary stereocenter using cinchona alkaloid-derived phthalazine as the catalyst. Various chlorinated 2, 2-disubstituted morpholines are achieved from alkenol substrates in excellent yields and enantioselectivities under mild conditions.