Asymmetric Synthesis ofanti-1,2-Amino Alcohols via the Borono-Mannich Reaction:  A Formal Synthesis of (−)-Swainsonine

2006 ◽  
Vol 71 (18) ◽  
pp. 7097-7099 ◽  
Author(s):  
Christopher W. G. Au ◽  
Stephen G. Pyne
Keyword(s):  
Asymmetric Synthesis ◽  
Mannich Reaction ◽  
Amino Alcohols ◽  
Formal Synthesis

scholarly journals Highly Enantioselective Synthesis of Fluorinated γ-Amino Alcohols Through Proline-Catalyzed Cross-Mannich Reaction.

ChemInform ◽  
2005 ◽  
Vol 36 (48) ◽  
Author(s):  
Santos Fustero ◽  
Diego Jimenez ◽  
Juan F. Sanz-Cervera ◽  
Maria Sanchez-Rosello ◽  
Elisabet Esteban ◽  
...  
Keyword(s):  
Mannich Reaction ◽  
Amino Alcohols ◽  
Enantioselective Synthesis

Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction

Science ◽  
2018 ◽  
Vol 360 (6396) ◽  
pp. 1438-1442 ◽  
Author(s):  
Jianfeng Chen ◽  
Xing Gong ◽  
Jianyu Li ◽  
Yingkun Li ◽  
Jiguo Ma ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
High Activity ◽  
Asymmetric Catalysis ◽  
Carbonyl Group ◽  
Mannich Reaction ◽  
Primary Amine ◽  
Chiral Amines ◽  
Carbonyl Groups ◽  
Diphenylphosphinyl Imines

Chiral amines are widely used as catalysts in asymmetric synthesis to activate carbonyl groups for α-functionalization. Carbonyl catalysis reverses that strategy by using a carbonyl group to activate a primary amine. Inspired by biological carbonyl catalysis, which is exemplified by reactions of pyridoxal-dependent enzymes, we developed an N-quaternized pyridoxal catalyst for the asymmetric Mannich reaction of glycinate with aryl N-diphenylphosphinyl imines. The catalyst exhibits high activity and stereoselectivity, likely enabled by enzyme-like cooperative bifunctional activation of the substrates. Our work demonstrates the catalytic utility of the pyridoxal moiety in asymmetric catalysis.

Chiral β-Amino Alcohols and Derivatives in the Asymmetric Synthesis of Tetrahydroisoquinolines

ChemInform ◽  
2004 ◽  
Vol 35 (31) ◽  
Author(s):  
Eneritz Anakabe ◽  
Dolores Badia ◽  
Luisa Carrillo ◽  
Efraim Reyes ◽  
Jose L. Vicario
Keyword(s):  
Asymmetric Synthesis ◽  
Amino Alcohols

scholarly journals Catalytic asymmetric formal synthesis of beraprost

2015 ◽  
Vol 11 ◽  
pp. 2654-2660 ◽  
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.

Sign in / Sign up

Export Citation Format

Share Document