The Diastereoselective Synthesis of Ester-Functionalized Alkenes through the Stereocontrolled Conjugate Addition (Michael Reaction) of Prochiral Enolates to Chiral .alpha.-Methylene .beta.-Lactones and Thermal Decarboxylation of the Resulting .alpha.-Substituted .beta.-Lactones

1995 ◽  
Vol 60 (12) ◽  
pp. 3879-3886 ◽  
Author(s):  
Victor Oswaldo Nava-Salgado ◽  
Eva-Maria Peters ◽  
Karl Peters ◽  
Hans Georg von Schnering ◽  
Waldemar Adam
Keyword(s):  
Michael Reaction ◽  
Conjugate Addition ◽  
Diastereoselective Synthesis ◽  
Thermal Decarboxylation

scholarly journals Photoredox radical conjugate addition of dithiane-2-carboxylate promoted by an iridium(iii) phenyl-tetrazole complex: a formal radical methylation of Michael acceptors

2017 ◽  
Vol 8 (2) ◽  
pp. 1613-1620 ◽  
Author(s):  
Andrea Gualandi ◽  
Elia Matteucci ◽  
Filippo Monti ◽  
Andrea Baschieri ◽  
Nicola Armaroli ◽  
...  
Keyword(s):  
Michael Reaction ◽  
Conjugate Addition ◽  
Michael Acceptors

An iridium(iii) phenyl-tetrazole complex is a versatile catalyst for a new photocatalytic Michael reaction.

scholarly journals Diastereoselective synthesis of pyridyl substituted thiazolidin-4-ones. New ligands for the Cu(I) catalyzed asymmetric conjugate addition of diethylzinc to enones

1997 ◽  
Vol 8 (10) ◽  
pp. 1539-1543 ◽  
Author(s):  
André H.M. de Vries ◽  
Robert P. Hof ◽  
Danny Staal ◽  
Richard M. Kellogg ◽  
Ben L. Feringa
Keyword(s):  
Conjugate Addition ◽  
Diastereoselective Synthesis

Diastereoselective Synthesis of Bicyclo[2.2.2]octan-2-one Derivatives through an Unexpected Organocatalytic Tandem Michael-Michael Reaction

Synthesis ◽  
2011 ◽  
Vol 2011 (12) ◽  
pp. 1984-1987 ◽  
Author(s):  
Jinxing Ye ◽  
Juanjuan Yang ◽  
Huicai Huang ◽  
Zhichao Jin ◽  
Wenbin Wu
Keyword(s):  
Michael Reaction ◽  
Diastereoselective Synthesis

Iodotrimethylsilane Induced Diastereoselective Synthesis of Tetrahydropyranones by a Tandem Knoevenagel—Michael Reaction.

ChemInform ◽  
2003 ◽  
Vol 34 (52) ◽  
Author(s):  
Gowravaram Sabitha ◽  
G. S. Kiran Kumar Reddy ◽  
M. Rajkumar ◽  
J. S. Yadav ◽  
K. V. S. Ramakrishna ◽  
...  
Keyword(s):  
Michael Reaction ◽  
Diastereoselective Synthesis

Approach to the Core Structure of 15-epi-Exiguolide

Synthesis ◽  
2018 ◽  
Vol 50 (16) ◽  
pp. 3131-3145 ◽  
Author(s):  
Martin Maier ◽  
Alexander Riefert
Keyword(s):  
Michael Reaction ◽  
Chain Extension ◽  
Reductive Cyclization ◽  
Unsaturated Ester ◽  
Pyran Ring ◽  
The Core ◽  
Synthetic Strategy ◽  
Propargylic Alcohol ◽  
Key Features ◽  
Thermal Decarboxylation

The synthesis of seco acid 41 of the macrolactone part of 15-epi-exiguolide, containing a bis-pyran subunit and a trans double bond, is described. Key features of the synthetic strategy include a Feringa–Minnaard asymmetric organocuprate addition to unsaturated ester 17 to set the stereocenter at C15. The derived acid 8 (C9–C16 fragment) was ideally suited for combination with aldehyde 9 (C17–C21 fragment) via an aldol strategy leading to β-lactone 25 which upon thermal decarboxylation provided alkene 26. Chain extension led to propargylic alcohol 7. Treatment of 7 with a LAu+ catalyst promoted a Meyer–Schuster rearrangement to enone 30 that led to cis-tetrahydropyran 31 via intramolecular oxa-Michael reaction. The second pyran ring was prepared from alkoxy ketone 5 by reductive cyclization. The further steps toward macrolactone 43 were hampered by the epimeric mixture at C5.

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