Asymmetric Quadruple Aminocatalytic Domino Reactions to Fused Carbocycles Incorporating a Spirooxindole Motif

Jiang, Kun; Jia, Zhijun; Yin, Xiang; Wu, Li; Chen, Ying‐Chun

doi:10.1021/ol100857s

Cited by 190 publications

(37 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Recently, cyclobutenones 323 Recently, chiral N -arylnitrones 327 and 328 were used with carbocyclic alkylarylketenes 326 in a pericyclic cascade comprising [3+2]-cycloaddition followed by a [3,3]sigmatropic rearrangement process to generate spirocyclic oxindoles 329 and 330 in good yields and with excellent levels of enantioselectivity (90-99 % ee) (Scheme 95) [187].…”

Section: Methods Of Spiro[cyclohexane-1 3-indoline]-2-one Framework mentioning

confidence: 99%

Molecular diversity of spirooxindoles. Synthesis and biological activity

et al. 2015

View full text Add to dashboard Cite

Spirooxindoles are important synthetic targets possessing extended biological activity and drug discovery applications. This review focuses on the various strategies for the enantioselective synthesis of spirocyclic oxindoles relying on reports over the past decade and from earlier work. The spirooxindoles in this review are separated into three structural classes, and then further categorized into the method type from which the spirocycle is generated.

show abstract

Section: Methods Of Spiro[cyclohexane-1 3-indoline]-2-one Framework mentioning

confidence: 99%

Molecular diversity of spirooxindoles. Synthesis and biological activity

et al. 2015

View full text Add to dashboard Cite

show abstract

“…[142] According to a Michael-Michael-Michael-aldol sequence, the process provided the corresponding almost enantio-and diastereopure complex fused tetracyclic products 302a-f bearing six contiguous stereogenic centers in moderate to excellent yields (30-97%), as shown in Scheme 79. The authors have proposed a quadruple iminium-enamine-iminium-enamine catalysis to explain the results.…”

Section: Michael Reaction Of Ab-unsaturated Aldehydesmentioning

confidence: 99%

Recent Developments in Asymmetric Organocatalytic Domino Reactions

2012

View full text Add to dashboard Cite

Since about the year 2000, the research area of asymmetric organocatalysis has grown rapidly to become one of the most fascinating and current fields in organic chemistry. In the last years, asymmetric domino reactions have widely benefited from this fast-growing field, as exemplified by the development of an explosive number of novel and powerful asymmetric organocatalytic domino processes, which allowed the easy construction of complex chiral molecular architectures from simple materials with high yields and very often remarkable enantioselectivities in a metal-free environment. Indeed, the possibility to join two or more organocatalytic reactions in one asymmetric domino process has become a challenging goal for chemists, due to several advantages from economical and environmental points of view, avoiding costly protecting groups and time-consuming purification procedures after each step, for example. This review aims to update the latest developments of this hot and fascinating field, covering the literature since the beginning of 2009.

show abstract

“…Brenner and McGarraugh reported the intermolecular synthesis of the hexahydro‐1 H ‐indene motif through double Michael reactions between enals and β‐keto esters having a cyclopentene moiety (Scheme ) . Also, Chen and co‐workers applied an aminocatalytic domino strategy for the synthesis of fused carbocycles with a spirooxindole motif (Scheme ) . We also recently reported the stepwise synthesis of 1‐decalone and hexahydro‐1 H ‐inden‐4(2 H )‐one structures through a dienamine‐catalyzed Michael reaction followed by 1,1,3,3‐tetramethylguanidine‐mediated cyclization, in which 1‐acetylcyclohexenes and 1‐acetylcyclopentenes were employed; however, the products were obtained with moderate enantioselectivities.…”

Section: Introductionmentioning

confidence: 99%