Organocatalytic Asymmetric Mannich Reaction of 3-Hydroxyoxindoles/3-Aminooxindoles with in Situ Generated N-Boc-Protected Aldimines for the Synthesis of Vicinal Oxindole-Diamines/Amino Alcohols.
A highly efficient asymmetric Mannich reaction of 3-monosubstituted 3-aminooxindoles/3-hydroxyoxindoles with in situ generated N-Boc-protected aldimines catalyzed by the chiral bifunctional thiourea-tertiary amine catalyst has been developed. Under mild reaction conditions, a series of structurally diverse vicinal oxindole-diamines/amino alcohols were smoothly obtained in moderate to high yields (up to 99%) with good to excellent diastereoselectivities and enantioselectivities (up to 95:5 dr and 96% ee). The synthetic application of this protocol was also demonstrated by the versatile transformation of chiral vicinal oxindole-diamine/amino alcohol into spirocyclic oxindoles.
School of Pharmacy, Zunyi Medical University , Zunyi 563000, P. R. China.
Jing
J
Shan
School of Pharmacy, Zunyi Medical University , Zunyi 563000, P. R. China.
Baodong
B
Cui
School of Pharmacy, Zunyi Medical University , Zunyi 563000, P. R. China.
Yu
Y
Wang
School of Pharmacy, Zunyi Medical University , Zunyi 563000, P. R. China.
Chengli
C
Yang
School of Pharmacy, Zunyi Medical University , Zunyi 563000, P. R. China.
Xiaojian
X
Zhou
School of Pharmacy, Zunyi Medical University , Zunyi 563000, P. R. China.
Wenyong
W
Han
School of Pharmacy, Zunyi Medical University , Zunyi 563000, P. R. China.
Yongzheng
Y
Chen