Organocatalytic Asymmetric Synthesis of 3-Chlorooxindoles Bearing Adjacent Quaternary-Tertiary Centers

被引：83

作者：

Noole, Artur ^{[1
]}

Jaerving, Ivar ^{[1
]}

Werner, Franz ^{[1
]}

Lopp, Margus ^{[1
]}

Malkov, Andrei ^{[2
]}

Kanger, Tonis ^{[1
]}

机构：

[1] Tallinn Univ Technol, Dept Chem, EE-12618 Tallinn, Estonia

[2] Univ Loughborough, Dept Chem, Loughborough LE11 3TU, Leics, England

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 18期

关键词：

MICHAEL ADDITION; OXINDOLES; 3-HYDROXY-2-OXINDOLES; 1,4-ADDITIONS; NITROALKENES; FLUORINATION;

D O I：

10.1021/ol302245b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new methodology was developed for the synthesis of enantiomerically enriched 3,3-disubstituted 3-chlorooxindoles 3 via a Michael addition of 3-chloroxindoles to nitroolefins 2, catalyzed by chiral squaramide 10. Products with adjacent quaternary-tertiary centers were isolated in excellent yields (up to 99%), high diastereoselectivities (up to 11:1), and enantiomeric purities (up to 92%). This is the first example where 3-chlorozoindoles 1 have been used as nucleophiles in a highly stereoselective organocatalytic reaction.

引用

页码：4922 / 4925

页数：4

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