Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition

2007 ◽  
Vol 5 (12) ◽  
pp. 1961 ◽  
Author(s):  
Stephen G. Davies ◽  
A. Christopher Garner ◽  
Euan C. Goddard ◽  
Dennis Kruchinin ◽  
Paul M. Roberts ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Conjugate Addition ◽  
Lithium Amide

Asymmetric Synthesis of 3,4-anti- and 3,4-syn-Substituted Aminopyrrolidines via Lithium Amide Conjugate Addition.

ChemInform ◽  
2007 ◽  
Vol 38 (44) ◽  
Author(s):  
Stephen G. Davies ◽  
A. Christopher Garner ◽  
Euan C. Goddard ◽  
Dennis Kruchinin ◽  
Paul M. Roberts ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Conjugate Addition ◽  
Lithium Amide

Asymmetric synthesis of β-substituted Baylis–Hillman products via lithium amide conjugate addition

Tetrahedron ◽  
2007 ◽  
Vol 63 (30) ◽  
pp. 7036-7046 ◽  
Author(s):  
Alexander Chernega ◽  
Stephen G. Davies ◽  
Dirk. L. Elend ◽  
Christian A.P. Smethurst ◽  
Paul M. Roberts ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Conjugate Addition ◽  
Lithium Amide

Asymmetric synthesis of 4-amino-γ-butyrolactones via lithium amide conjugate addition

Tetrahedron ◽  
2007 ◽  
Vol 63 (26) ◽  
pp. 5855-5872 ◽  
Author(s):  
Elin Abraham ◽  
Jason W.B. Cooke ◽  
Stephen G. Davies ◽  
Alan Naylor ◽  
Rebecca L. Nicholson ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Conjugate Addition ◽  
Lithium Amide

scholarly journals Asymmetric Synthesis of Pyrrolizidines, Indolizidines and Quinolizidines via a Double Reductive Cyclisation Protocol

Synlett ◽  
2017 ◽  
Vol 28 (20) ◽  
pp. 2697-2706 ◽  
Author(s):  
Stephen Davies ◽  
Ai Fletcher ◽  
Paul Roberts ◽  
James Thomson
Keyword(s):  
Asymmetric Synthesis ◽  
Conjugate Addition ◽  
Unsaturated Ester ◽  
Asymmetric Syntheses ◽  
Lithium Amide ◽  
Target Molecule

This account describes an overview of the asymmetric syntheses of pyrrolizidines, indolizidines and quinolizidines via a common double reductive cyclisation protocol. The highly diastereoselective conjugate addition of an enantiopure lithium amide to an α,β-unsaturated ester incorporating a terminal C=C bond installed the nitrogen-bearing stereogenic centre and was followed by enolate functionalisation to introduce the second olefinic functionality. Alternatively, conjugate addition to the corresponding α-alkenyl α,β-unsaturated ester followed by α-protonation of the intermediate enolate may also be used to access the cyclisation precursor. After oxidation of the two terminal olefinic units to give the corresponding dialdehyde, tandem hydrogenolysis/hydrogenation was employed to efficiently construct the azabicyclic core of each target molecule. This double reductive cyclisation strategy was successfully utilised in the syntheses of 13 azabicyclic alkaloids or closely related analogues.1 Introduction2 Asymmetric Syntheses of (–)-Isoretronecanol and (–)-Trachelanthamidine3 Asymmetric Syntheses of (+)-Trachelanthamidine [(+)-Laburnine], (+)-Tashiromine and (+)-epi-Lupinine4 Asymmetric Syntheses of (–)-Hastanecine, (–)-Turneforcidine and (–)-Platynecine5 Asymmetric Syntheses of (–)-Macronecine, (–)-Petasinecine, (–)-1-epi-Macronecine, (+)-1-epi-Petasinecine and (+)-2-epi-Rosmarinecine6 Conclusion

ChemInform Abstract: Asymmetric Synthesis of Sedum Alkaloids via Lithium Amide Conjugate Addition.

ChemInform ◽  
2010 ◽  
Vol 41 (13) ◽  
Author(s):  
Stephen G. Davies ◽  
Ai M. Fletcher ◽  
Paul M. Roberts ◽  
Andrew D. Smith
Keyword(s):  
Asymmetric Synthesis ◽  
Conjugate Addition ◽  
Lithium Amide

Asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition

2008 ◽  
Vol 6 (9) ◽  
pp. 1665 ◽  
Author(s):  
Elin Abraham ◽  
E. Anne Brock ◽  
José I. Candela-Lena ◽  
Stephen G. Davies ◽  
Matthew Georgiou ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Conjugate Addition ◽  
Lithium Amide ◽  
Jaspine B

Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition

Tetrahedron ◽  
2009 ◽  
Vol 65 (49) ◽  
pp. 10192-10213 ◽  
Author(s):  
Stephen G. Davies ◽  
Ai M. Fletcher ◽  
Paul M. Roberts ◽  
Andrew D. Smith
Keyword(s):  
Asymmetric Synthesis ◽  
Conjugate Addition ◽  
Lithium Amide

Asymmetric Synthesis of 4-Amino-γ-butyrolactones via Lithium Amide Conjugate Addition.

ChemInform ◽  
2007 ◽  
Vol 38 (40) ◽  
Author(s):  
Elin Abraham ◽  
Jason W. B. Cooke ◽  
Stephen G. Davies ◽  
Alan Naylor ◽  
Rebecca L. Nicholson ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Conjugate Addition ◽  
Lithium Amide

Lithium Amide Conjugate Addition for the Asymmetric Synthesis of 3-Aminopyrrolidines.

ChemInform ◽  
2006 ◽  
Vol 37 (45) ◽  
Author(s):  
Stephen G. Davies ◽  
A. Christopher Garner ◽  
Euan C. Goddard ◽  
Dennis Kruchinin ◽  
Paul M. Roberts ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Conjugate Addition ◽  
Lithium Amide
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