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Catalytic Asymmetric [4+1] Cyclization of ortho ‐Quinone Methides with 3‐Chlorooxindoles
Author(s) -
Jiang XiaoLi,
Liu SiJia,
Gu YuQi,
Mei GuangJian,
Shi Feng
Publication year - 2017
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.201700487
Subject(s) - chemistry , enantioselective synthesis , catalysis , yield (engineering) , domino , combinatorial chemistry , stereoselectivity , quinone , stereochemistry , medicinal chemistry , organic chemistry , metallurgy , materials science
In this work, we established catalytic asymmetric [4+1] cyclization of ortho ‐quinone methides ( o ‐QMs) with 3‐chlorooxindoles and a catalytic asymmetric domino oxidation/[4+1] cyclization reaction of 2‐alkylphenols with 3‐chlorooxindoles, which constructed a spirooxindole‐based 2,3‐dihydrobenzofuran scaffold in good yield (up to 97%), with excellent diastereoselectivity (up to >95:5 dr ) and high enantioselectivity (up to 99% ee ). This work is not only the first highly enantioselective [4+1] cyclization of o ‐QMs but has also realized the first catalytic asymmetric domino [4+1] cyclization of o ‐QMs. In addition, both of the reactions provide efficient stereoselective methods for constructing spirooxindole‐based 2,3‐dihydrobenzofuran scaffolds with optical purity.