Organocatalytic Enantioselective Intramolecular Michael Addition by In Situ Generated Aminoisobenzofulvenes: Construction of Spiro Quaternary Carbon Stereocenters

被引：1
|
作者：
Midya, Abhisek [1 ]
Khalse, Laxman Devidas [1 ]
Ghorai, Prasanta [1 ]
机构：
[1] Indian Inst Sci Educ & Res IISER Bhopal, Dept Chem, Bhopal By Pass Rd, Bhopal 462066, India
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2023年 / 29卷 / 59期
关键词：
all carbon quaternary stereocenter; enamine-iminum catalysis; Michael addition; organocatalysis; spirocyclization; DIARYLPROLINOL SILYL ETHERS; TRANSFER HYDROGENATION; NATURAL-PRODUCTS; CYCLOADDITION REACTIONS; ASYMMETRIC-SYNTHESIS; DOMINO REACTIONS; METAL-FREE; REARRANGEMENT; CASCADE; ESTERS;
D O I：
10.1002/chem.202301563
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An unprecedented enantioselective organocatalytic spirocyclization strategy is presented by in situ generation of aminoisobezofulvenes. The reaction sequence involves a reductive Michael/aldol-condensation/Michael addition cascade by iminium-enamine catalysis. The key success of this spirocyclization was the formation of intermediatory nucleophilic aminoisobenzofuvenes accountable for intramolecular Michael addition. Benzospirononanes featuring an all carbon qauternary spirocenter were obtained using proline-derived amino-organocatalyst in moderate to good yields and excellent diastereo- and enantioselectivities (up to >20 : 1 dr, and 99 % ee). Post-methodological manipulation of benzospirononanes was also demonstrated.
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页数：6
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