Beilstein J. Org. Chem.2019,15, 1984–1995, doi:10.3762/bjoc.15.194
the formal synthesis of triptolide (Figure 2, route N) [43]. This synthesis highlighted the palladium-catalyzed asymmetric addition of arylboronic acid 37 to 3-methylcyclohex-2-en-1-one (38) to form the C-10 quaternarychiralcenter, and a subsequent Claisen rearrangement and an aldol reaction to
Beilstein J. Org. Chem.2012,8, 1241–1245, doi:10.3762/bjoc.8.139
yields (up to 97%).
Keywords: allylic amination; asymmetric organocatalysis; Morita–Baylis–Hillman carbonates; 2-oxindoles; quaternarychiralcenter; Introduction
Chiral 3-amino-2-oxindoles are versatile and useful units for the preparation of natural products and drug candidates, such as the
isatins to obtain 2-oxindoles bearing a C3-quaternarychiralcenter, by the catalysis of chiral tertiary amines, β-isocupreidine (β-ICD) or its derivatives [23][24]. We envisaged that such a catalytic strategy should be applicable to the allylic amination of the corresponding MBH carbonates [25][26][27
provides an electrophilic process to 3-amino-2-oxindoles with a C3-quaternarychiralcenter. A range of products with high molecular complexity were obtained with good to excellent enantioselectivity (up to 94% ee) and high yields (up to 97%). Currently, more studies on the catalytic asymmetric
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Graphical Abstract
Scheme 1:
Allylic amination of MBH carbonates of isatins to access 3-amino-2-oxindoles.