ChemInform Abstract: Recyclable Organocatalyst-Promoted One-Pot Michael/Aza-Henry/Lactamization Reactions for Fluorinated 2-Piperidinones Bearing Four Stereogenic Centers.

The first example of a bifunctional donor–donor 3C synthon formed in situ from an activated methine with nitromethane through a [2+1] Michael addition, further directing a one-pot organocascade Michael/Henry cycloaddition was developed.

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One-Pot Asymmetric Synthesis of β-Cyanohydroxymethyl α-Amino Acid Derivatives: Formation of Three Contiguous Stereogenic Centers

Organic Letters ◽

10.1021/ol027048x ◽

2002 ◽

Vol 4 (25) ◽

pp. 4519-4522 ◽

Cited By ~ 42

Author(s):

Shin-ichi Watanabe ◽

Armando Córdova ◽

Fujie Tanaka ◽

Carlos F. Barbas

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis ◽

Amino Acid Derivatives ◽

One Pot ◽

Stereogenic Centers

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Cationic Cascade for Building Complex Polycyclic Molecules from Simple Precursors: Diastereoselective Installation of Three Contiguous Stereogenic Centers in a One-Pot Process

Journal of the American Chemical Society ◽

10.1021/jacs.8b11713 ◽

2018 ◽

Vol 141 (1) ◽

pp. 118-122 ◽

Cited By ~ 11

Author(s):

Georgios Alachouzos ◽

Alison J. Frontier

Keyword(s):

One Pot ◽

Stereogenic Centers

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Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters

Chemical Communications ◽

10.1039/c4cc09730k ◽

2015 ◽

Vol 51 (12) ◽

pp. 2270-2272 ◽

Cited By ~ 41

Author(s):

Pankaj Chauhan ◽

Suruchi Mahajan ◽

Gerhard Raabe ◽

Dieter Enders

Keyword(s):

Addition Reaction ◽

One Pot ◽

Stereogenic Centers

A new stereoselective organocatalyzed one-pot 1,4-/1,6-/1,2-addition reaction sequentially catalyzed by low loading of a squaramide and an achiral base provide a direct entry to isoxazole bearing cyclohexanes with six contiguous stereogenic centers in good yields and excellent stereoselectivities.

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An Intramolecular Diels–Alder Furan (IMDAF) Approach towards the Synthesis of Isoindolo[2,1-a]quinazolines and Isoindolo[1,2-b]quinazolines

Synthesis ◽

10.1055/s-0036-1588812 ◽

2017 ◽

Vol 49 (16) ◽

pp. 3749-3767 ◽

Cited By ~ 5

Author(s):

Vladimir Zaytsev ◽

Ekaterina Revutskaya ◽

Tatiana Nikanorova ◽

Eugeniya Nikitina ◽

Pavel Dorovatovskii ◽

...

Keyword(s):

Unsaturated Acid ◽

Nitrogen Heterocycles ◽

Diels Alder ◽

Isatoic Anhydride ◽

One Pot ◽

Efficient Approach ◽

Condensation Reactions ◽

Stereogenic Centers ◽

Acid Anhydrides

An efficient approach to bridged pentacyclic nitrogen heterocycles via the tandem acylation/intramolecular Diels–Alder furan (IMDAF) reaction of 2-furylquinazolinones is described. Reactions of α,β-unsaturated acid anhydrides with 2-furyl-2,3-dihydroquinazolin-4-ones give 6b,9-epoxyisoindolo[2,1-a]quinazolines in average yields. In this case, the exo-IMDAF reactions proceed with excellent diastereoselectivity giving five stereogenic centers and three new rings in one synthetic step. Isomeric 2,4a-epoxyisoindolo[1,2-b]quinazolines are obtained by one-pot, three-component condensation reactions of allylamine, isatoic anhydride and furaldehydes involving the same IMDAF reaction as the key step. Some useful transformations including halogenation, hydrogenation, Prilezhaev epoxidation, and esterification of the synthesized epoxyisoindoloquinazolines are also demonstrated.

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