Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 16, Pages 4372-4378Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo00390b
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- Guangzhou Basic and Applied Basic Research Foundation [202102080114]
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A catalytic asymmetric halocyclization protocol has been developed to synthesize morpholines containing a quaternary stereocenter. Various chlorinated 2,2-disubstituted morpholines were obtained in excellent yields and enantioselectivities under mild conditions using cinchona alkaloid-derived phthalazine as the catalyst.
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.
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