0000000000826610
AUTHOR
Tao Shu
Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction.
An NHC-catalyzed Michael/Michael/esterification domino reaction via homoenolate/enolate intermediates for the asymmetric synthesis of tetrasubstituted cyclopentanes is described.
ChemInform Abstract: Asymmetric Synthesis of Cyclopentanes Bearing Four Contiguous Stereocenters via an NHC-Catalyzed Michael/Michael/Esterification Domino Reaction.
An NHC-catalyzed Michael/Michael/esterification domino reaction via homoenolate/enolate intermediates for the asymmetric synthesis of tetrasubstituted cyclopentanes bearing four contiguous stereocenters is described. A variety of α,β-unsaturated aldehydes and 2-nitroallylic acetates react well with good domino yields and high stereoselectivities.
Asymmetric synthesis of functionalized tetrahydrofluorenones via an NHC-catalyzed homoenolate Michael addition
The first example of an N-heterocyclic carbene-catalyzed asymmetric desymmetrization of enal-tethered cyclohexadienones via an intramolecular homoenolate Michael addition/esterification reaction is described. This new protocol offers a direct entry to various functionalized tetrahydrofluorenones with three contiguous stereocenters in high yields, good diastereoselectivities and excellent enantioselectivities.
Asymmetric Synthesis of Spirocyclic β-Lactams through Copper-Catalyzed Kinugasa/Michael Domino Reactions
The first copper-catalyzed highly chemo-, regio-, diastereo-, and enantioselective Kinugasa/Michael domino reaction for the desymmetrization of prochiral cyclohexadienones is described. In the presence of a chiral copper catalyst, alkyne-tethered cyclohexadienones couple with nitrones to generate the chiral spirocyclic lactams with excellent stereoselectivity (up to 97 % ee, >20:1 dr). The new method provides direct access to versatile highly functionalized spirocyclic β-lactams possessing four contiguous stereocenters, including one quaternary and one tetra-substituted stereocenter.
Asymmetric Synthesis of Spirocyclic β‐Lactams via Copper‐Catalyzed Kinugasa/Michael Domino Reactions
The first copper‐catalyzed highly chemo‐, regio‐, diastereo‐, and enantioselective Kinugasa/Michael domino reaction for the desymmetrization of prochiral cyclohexadienones is described. In the presence of a chiral copper catalyst, alkyne‐tethered cyclohexadienones couple with nitrones to generate the chiral spirocyclic lactams with excellent stereoselectivity (up to 97 % ee, >20:1 dr). The new method provides direct access to versatile highly functionalized spirocyclic β‐lactams possessing four contiguous stereocenters, including one quaternary and one tetra‐substituted stereocenter. peerReviewed
Organocatalytic Domino Oxa-Michael/1,6-Addition Reactions: Asymmetric Synthesis of Chromans Bearing Oxindole Scaffolds.
An asymmetric organocatalytic domino oxa-Michael/1,6-addition reaction of ortho-hydroxyphenyl-substituted para-quinone methides and isatin-derived enoates has been developed. In the presence of 5 mol % of a bifunctional thiourea organocatalyst, this scalable domino reaction affords 4-phenyl-substituted chromans bearing spiro-connected oxindole scaffolds and three adjacent stereogenic centers in good to excellent yields (up to 98 %) and with very high stereoselectivities (up to >20:1 d.r., >99 % ee).
CCDC 1831622: Experimental Crystal Structure Determination
Related Article: Tao Shu, Long Zhao, Sun Li, Xiang-Yu Chen, Carolina von Essen, Kari Rissanen, Dieter Enders|2018|Angew.Chem.,Int.Ed.|57|10985|doi:10.1002/anie.201806931
CCDC 1437686: Experimental Crystal Structure Determination
Related Article: Tao Shu, Qijian Ni, Xiaoxiao Song, Kun Zhao, Tianyu Wu, Rakesh Puttreddy, Kari Rissanen, Dieter Enders|2016|Chem.Commun.|52|2609|doi:10.1039/C5CC09581F
CCDC 1493409: Experimental Crystal Structure Determination
Related Article: Kun Zhao, Ying Zhi, Tao Shu, Arto Valkonen, Kari Rissanen, Dieter Enders|2016|Angew.Chem.,Int.Ed.|55|12104|doi:10.1002/anie.201606947
CCDC 1844760: Experimental Crystal Structure Determination
Related Article: Tao Shu, Sun Li, Xiang-Yu Chen, Qiang Liu, Carolina von Essen, Kari Rissanen, Dieter Enders|2018|Chem.Commun.|54|7661|doi:10.1039/C8CC04145H