Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chirality

The asymmetric and catalytic Michael reaction between α-nitroesters and nitroalkenes has been studied in the presence of two bifunctional catalysts both containing the same absolute chirality at the carbon backbone. The reaction performed in similar conditions allows us to control the syn or anti selectivity of the Michael adduct obtaining good yields and high enantiocontrol in all cases.

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Catalytic asymmetric formal synthesis of beraprost

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.11.285 ◽

2015 ◽

Vol 11 ◽

pp. 2654-2660 ◽

Cited By ~ 11

Author(s):

Yusuke Kobayashi ◽

Ryuta Kuramoto ◽

Yoshiji Takemoto

Keyword(s):

Asymmetric Synthesis ◽

Michael Reaction ◽

Subsequent Reduction ◽

Formal Synthesis ◽

Michael Adduct ◽

Catalytic Asymmetric Synthesis ◽

Weinreb Amide ◽

Tricyclic Core ◽

Catalytic Asymmetric

The first catalytic asymmetric synthesis of the key intermediate for beraprost has been achieved through an enantioselective intramolecular oxa-Michael reaction of an α,β-unsaturated amide mediated by a newly developed benzothiadiazine catalyst. The Weinreb amide moiety and bromo substituent of the Michael adduct were utilized for the C–C bond formations to construct the scaffold. All four contiguous stereocenters of the tricyclic core were controlled via Rh-catalyzed stereoselective C–H insertion and the subsequent reduction from the convex face.

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ChemInform Abstract: Organocatalytic and Enantioselective Michael Reaction Between α-Nitroesters and Nitroalkenes. Syn/anti-Selectivity Control Using Catalysts with the Same Absolute Backbone Chirality.

ChemInform ◽

10.1002/chin.201610021 ◽

2016 ◽

Vol 47 (10) ◽

pp. no-no

Author(s):

Jose I. Martinez ◽

Uxue Uria ◽

Maria Muniz ◽

Efraim Reyes ◽

Luisa Carrillo ◽

...

Keyword(s):

Michael Reaction ◽

Selectivity Control

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Heterogeneous enantioselective synthesis of chromans via the oxa-Michael–Michael cascade reaction synergically catalyzed by grafted chiral bases and inherent hydroxyls on mesoporous silica surface

Chemical Communications ◽

10.1039/c7cc03556j ◽

2017 ◽

Vol 53 (63) ◽

pp. 8882-8885 ◽

Cited By ~ 19

Author(s):

Shanshan Wang ◽

Jing He ◽

Zhe An

Keyword(s):

Mesoporous Silica ◽

Michael Reaction ◽

Silica Surface ◽

Catalytic Performance ◽

Cascade Reaction ◽

Enantioselective Synthesis ◽

Bifunctional Catalysts ◽

Excellent Catalytic Performance

A heterogeneous enantioselective oxa-Michael–Michael reaction for the synthesis of chromans has been developed on bifunctional catalysts, resulting in excellent catalytic performance.

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