Petasis-Type gem-Difluoroallylation Reactions Assisted by the Neighboring Hydroxyl Group in Amines

作者：Yang, Xing; Cao, Ze-Hun; Zhou, Yang; Cheng, Feng; Lin, Zi-Wei; Ou, Zhi; Yuan, Ye; Huang, Yi-Yong^*

来源：Organic Letters, 2018, 20(9): 2585-2589.

DOI：10.1021/acs.orglett.8b00721

• STEP 3-COMPONENT REACTION
• BORONO-MANNICH REACTIONS
• CHIRAL PHOSPHORIC-ACID
• STEREOSELECTIVE-SYNTHESIS
• ORGANOBORONIC ACIDS
• STEREOCONTROLLED SYNTHESIS
• ENANTIOSELECTIVE SYNTHESIS
• ALPHA-AMINOALLYLATION
• ASYMMETRIC-SYNTHESIS
• DIPEPTIDE ISOSTERES

A three-component Petasis-type gem-difluoroallylation reaction of using pinacol gem-difluoroallylboronates, aldehydes or isatin, and beta-amino alcohols enabled by the neighboring hydroxyl group in amine is reported, affording various racemic and chiral gem-difluorohomoallylamine derivatives with good to excellent results. Based on the control experiment and stereochemistry of the product, a proposed reaction pathway is illustrated to clarify the origin of regio- and stereoselectivity under protic solvent conditions.

• 出版日期2018-5-4
• 单位武汉理工大学