Enantioselective Organocatalytic Domino Michael/Aldol Reactions: An Efficient Procedure for the Stereocontrolled Construction of 2<i>H</i>‐Thiopyrano[2,3‐b]quinoline Scaffolds

Wu, Lulu; Wang, Youming; Song, Haibin; Tang, Liang‐Fu; Tang, Chuchi

doi:10.1002/asia.201300450

Cited by 26 publications

(8 citation statements)

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“…Recently, Y. Wang, Zhou, and co-workers published an efficient domino sulfa-Michael/aldol reaction of 2-mercaptoquinoline-3-carbaldehydes 131 with enals 137 catalyzed by the diphenylprolinol TMS ether XLIII (Scheme 63). 98 74%) and high enantioselectivities (90−96% ee). However, when a base was used as an additive instead of an acid, diastereomerically pure isomeric tetrahydrothiophenes 155 were obtained in moderate yields (43−66%) and moderate to good enantioselectivities (64−80% ee).…”

Section: Amino Catalysis Via Iminium Activationmentioning

confidence: 99%

Organocatalytic Carbon–Sulfur Bond-Forming Reactions

2014

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Section: Amino Catalysis Via Iminium Activationmentioning

confidence: 99%

Organocatalytic Carbon–Sulfur Bond-Forming Reactions

2014

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“…The chiral pyrrolidine 110 catalyzed domino reactions between thiosalicylic aldehyde and α,β‐unsaturated aldehydes proceeded with high chemo‐ and enantioselectivities to give thiochromene‐3‐carbaldehyde 111 in high yields with 91–98 % ee . The substrates initially formed Michael/aldol products, which underwent spontaneous dehydration to afford chiral thiopyrano[2,3‐ b ]quinolines with one new stereocenter …”

Section: Benzaldo‐x Bifunctional Building Blocks and Their Heterocyclmentioning

confidence: 99%

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Ravichandiran

Lai

2016

The Chemical Record

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Compounds containing oxygen, nitrogen, or sulfur atoms inside the rings are attracting much attention and interest due to their biological importance. In recent years, several methods for the synthesis of such molecules have been reported by using aldo-X bifunctional building blocks (AXB3 s) as substrates; these are a wide class of organic molecules that contain at least two reactive sites, among them, one aldehyde, acetal, or semiacetal group was involved. Because of the multiple reactivities, AXB3 s are widely used in the one-pot synthesis of biologically important heterocycles. This review summarizes the synthesis of important heterocycles by using AXB3 s as pivotal components in establishing multicomponent reactions, tandem reactions, and so forth. In many cases, the established reaction systems with AXB3 s were characterized by some green properties, such as easy access to the substrate, mild and environmentally benign conditions, and wide scope of the substrate.

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“…Uniting unique activation modes of N-heterocyclic carbene (NHC) catalysts with the concept of domino reactions, a new fast-growing field came into the spotlight in last couple of years or so [267][268][269]. Domino Michael/aldol reaction between 2-mercaptoquinoline-3-carbaldehydes and enals was catalyzed by diphenylprolinol silyl ether producing 2H-thiopyrano[2,3-b]quinolines in excellent yields and enantioselectivities [270]. Zhao et al reported studies on "cooperative NHC and rutheniun redox catalysis" in the oxidative esterification of aldehydes [271].…”

Section: Oxazaborolidines Chiral Oxazaborolidines (Known Asmentioning

confidence: 99%

Organocatalysis: Key Trends in Green Synthetic Chemistry, Challenges, Scope towards Heterogenization, and Importance from Research and Industrial Point of View

Shaikh

2014

Journal of Catalysts

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This paper purports to review catalysis, particularly the organocatalysis and its origin, key trends, challenges, examples, scope, and importance. The definition of organocatalyst corresponds to a low molecular weight organic molecule which in stoichiometric amounts catalyzes a chemical reaction. In this review, the use of the termheterogenized organocatalystwill be exclusively confined to a catalytic system containing an organic molecule immobilized onto some sort of support material and is responsible for accelerating a chemical reaction. Firstly, a brief description of the field is provided putting it in a green and sustainable perspective of chemistry. Next, research findings on the use of organocatalysts on various inorganic supports including nano(porous)materials, nanoparticles, silica, and zeolite/zeolitic materials are scrutinized in brief. Then future scope, research directions, and academic and industrial applications will be outlined. A succinct account will summarize some of the research and developments in the field. This review tries to bring many outstanding researches together and shows the vitality of the organocatalysis through several aspects.

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Enantioselective Organocatalytic Domino Michael/Aldol Reactions: An Efficient Procedure for the Stereocontrolled Construction of 2H‐Thiopyrano[2,3‐b]quinoline Scaffolds

Cited by 26 publications

References 50 publications

Organocatalytic Carbon–Sulfur Bond-Forming Reactions

Organocatalytic Carbon–Sulfur Bond-Forming Reactions

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Organocatalysis: Key Trends in Green Synthetic Chemistry, Challenges, Scope towards Heterogenization, and Importance from Research and Industrial Point of View

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