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Recent Catalytic Asymmetric Syntheses of 3,3‐Disubstituted Indolin‐2‐ones and 2,2‐Disubstituted Indolin‐3‐ones
Author(s) -
Dalpozzo Renato
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.201700361
Subject(s) - chemistry , dabco , methanesulfonic acid , catalysis , stereochemistry , octane , organic chemistry , medicinal chemistry , combinatorial chemistry
Disubstituted oxindoles represent an important family of bioactive compounds and synthetic derivatives that mimic natural products. The construction of the asymmetric quaternary carbon at C‐3 or C‐2 is therefore a challenging problem for organic chemists. In the last years, many papers have appeared on asymmetric catalytic methods for the synthesis of these compounds, in particular about spirocyclic derivatives and this literature has been largely reviewed, as well as the literature on 3‐substituted‐3‐hydroxyoxindoles and 3‐substituted‐3‐aminooxindoles. On the other hand, the literature on non‐spirocyclic 3,3‐dialkyloxindoles as well as on 2,2‐disubstituted 3‐indolinones has not fully reviewed since our previous review on this topic. This review aims to fill this gap covering the literature on these topics. Abbreviations : Alloc=allyloxycarbonyl; Ant=anthracenyl; BINOL=1,1′‐binaphthalene‐2,2′‐diol; Boc= t ‐butoxycarbonyl; Bz=benzoyl; Cbz=benzyloxycarbonyl; CSA=camphorsulfonic acid; Cy=cyclohexyl; DABCO=1,4‐diazabicyclo[2.2.2]octane; dba=bis(dibenzylideneacetone); DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene; DDQ=2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone; (DHQD) 2 AQN=hydroquinidine (anthraquinone‐1,4‐diyl) diether; (DHQD) 2 PHAL=hydroquinidine 1,4‐phthalazinediyl diether; (DHQD) 2 PYR=hydroquinidine 2,5‐diphenyl‐4,6‐pyrimidinediyl diether; DIPEA= N , N ‐diisopropylethylamine; esp=α,α,α′,α′‐tetramethyl‐1,3‐benzenedipropionic acid; HFIP=1,1,1,3,3,3‐hexafluoro‐2‐propanol; HMDS=hexamethyldisilazane; β‐ICD=β‐isocupreidine; LG=leaving group; Mes=2,4,6‐trimethylphenyl; Moc=methoxycarbonyl; MOM=methoxymethyl; MS=molecular sieves; MsOH=methanesulfonic acid; NHC=N‐heterocyclic carbene; Npt=naphthyl; PG=protecting group; Phg=phenylglycine; Phth=phthalimidyl; Piv=2,2‐dimethylpropanoyl; PMB=4‐methoxybenzyl; Red‐Al=sodium bis(2‐methoxyethoxy)aluminium hydride; Suc=succinimidyl; TBDPS= tert ‐butyldiphenylsilyl; TBS= tert ‐butyldimethylsilyl; TES=triethylsilyl; TIPS=triisopropylsilyl; TMEDA= N , N , N′,N′ ‐tetramethylethylenediamine; TMG=1,1,3,3‐tetramethylguanidine; TMS=trimethylsilyl; Ts=4‐toluenesulfonyl.