Yayınlanmış 1 Ocak 2020 | Sürüm v1
Dergi makalesi Açık

Bifunctional squaramide catalyzed stereoselective Mannich reaction of alpha-azido ketones with isatin-derived ketimines

  • 1. Middle East Tech Univ, Dept Chem, TR-06800 Ankara, Turkey

Açıklama

Asymmetric organocatalytic Mannich reaction of alpha-azido ketones and N-Boc protected isatin-derived ketimines were investigated for the first time. Examination of both 2-adamantyl and 3,5-bis(trifluoromethyl)aniline substituted quinine-based squaramides afforded chiral Mannich bases with two contiguous stereogenic centers in high yields (up to 97%) and stereoselectivity (up to dr = 24 : 1 syn : anti and 96% ee). Azido and masked amino functionalities of the potent heterocycle precursor adducts were utilized in representative examples.

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bib-a4c68b00-efd8-4f6b-af38-cb9e9475381f.txt

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