Chiral lithium amide base-mediated rearrangement of meso-cyclohexene oxides: asymmetric synthesis of amino- and aziridinocyclohexenols

2003 ◽  
Vol 1 (3) ◽  
pp. 523-534 ◽  
Author(s):  
Peter O'Brien ◽  
Christopher D. Pilgram
Keyword(s):  
Asymmetric Synthesis ◽  
Lithium Amide ◽  
Cyclohexene Oxides

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 2,3,6-Trisubstituted Piperidines via Baylis–Hillman Adducts and Lithium Amide through Domino Reaction

Synlett ◽  
2019 ◽  
Vol 31 (06) ◽  
pp. 600-604 ◽  
Author(s):  
Mateo M. Salgado ◽  
Alejandro Manchado ◽  
Carlos T. Nieto ◽  
David Díez ◽  
Narciso M. Garrido
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Claisen Rearrangement ◽  
Domino Reaction ◽  
Amino Acid Derivative ◽  
Side Chain ◽  
Lithium Amide ◽  
Stereochemical Control ◽  
Asymmetric Michael Addition ◽  
Polysubstituted Piperidines

A convenient asymmetric synthesis of methyl (2S,3S,6R)-6-(4-fluorophenyl)-2-(4-hydroxyphenyl)-piperidine-3-carboxylate is described, starting from Baylis–Hillman adducts. The route involves a domino process: allylic acetate rearrangement, stereoselective Ireland–Claisen rearrangement and asymmetric Michael addition, which provides a δ-amino acid derivative with full stereochemical control. A subsequent chemoselective transformation of one of the side-chain groups allows an effective cyclization leading to biologically interesting polysubstituted piperidines in which the 2,6-aryl groups could be attached sequentially.

Asymmetric synthesis of the erythrinan alkaloid system using a chiral lithium amide base desymmetrisation as the key step

2003 ◽  
Vol 44 (42) ◽  
pp. 7803-7807 ◽  
Author(s):  
Christopher Gill ◽  
Daniel A. Greenhalgh ◽  
Nigel S. Simpkins
Keyword(s):  
Asymmetric Synthesis ◽  
Lithium Amide ◽  
Erythrinan Alkaloid

scholarly journals α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines

2010 ◽  
Vol 6 ◽  
pp. 978-983 ◽  
Author(s):  
David M Hodgson ◽  
Zhaoqing Xu
Keyword(s):  
Asymmetric Synthesis ◽  
Lithium Amide ◽  
Group Migration

N-Phosphonate terminal aziridines undergo lithium 2,2,6,6-tetramethylpiperidide-induced N- to C-[1,2]-anionic phosphonyl group migration under experimentally straightforward conditions, to provide a stereocontrolled access to synthetically valuable trans-α,β-aziridinylphosphonates. The utility of this chemistry has been demonstrated in the asymmetric synthesis of a β-aminophosphonate.

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

ChemInform Abstract: Asymmetric Synthesis Using Homochiral Lithium Amide Bases

ChemInform ◽  
2010 ◽  
Vol 22 (24) ◽  
pp. no-no
Author(s):  
P. J. COX ◽  
N. S SIMPKINS
Keyword(s):  
Asymmetric Synthesis ◽  
Lithium Amide
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