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C 3 ‐Symmetric Cinchonine‐Squaramide‐Catalyzed Asymmetric Chlorolactonization of Styrene‐Type Carboxylic Acids with 1,3‐Dichloro‐5,5‐dimethylhydantoin: An Efficient Method to Chiral Isochroman‐1‐ones
Author(s) -
Han Xin,
Dong Chune,
Zhou HaiBing
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300915
Subject(s) - chemistry , cinchonine , squaramide , yield (engineering) , catalysis , styrene , enantioselective synthesis , cinchonidine , organic chemistry , combinatorial chemistry , medicinal chemistry , organocatalysis , copolymer , materials science , polymer , metallurgy
A more practical and efficient catalytic asymmetric chlorolactonization of styrene‐type carboxylic acids with 1,3‐dichloro‐5,5‐dimethylhydantoin (DCDMH) using C 3 ‐symmetric cinchonine‐squaramide (CSCS) as organocatalyst has been developed. A series of chiral chloro‐substituted isochroman‐1‐ones was obtained in excellent yields (up to 95%) and enantioselectivities (up to 99% ee ), whwereby the results for chloro‐substituted isochroman‐1‐ones are the best ever achieved. The catalyst can be recovered and reused for six cycles. Moreover, the chlorolactonization product 3b was further transformed to optically active bicyclic isochroman‐1‐one derivatives in high yield without losing the enantioselectivity. Furthermore, compounds 3e and 2n proved to be highly potent inhibitors of the HIV‐1 in TZM‐bl cells.