Rapid access to cis-cyclobutane γ-amino acids in enantiomerically pure form

The (+)-(1 R,2 S) and (−)-(1 S,2 R) stereoisomers of 2-(aminomethyl)cyclobutane-1-carboxylic acid have been prepared using a short and efficient strategy, which employs the photochemical [2+2] cycloaddition reaction between ethylene and an unsaturated γ-lactam as the key step.

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Bibliographische Detailangaben
Veröffentlicht in:	Tetrahedron letters 2011-03, Vol.52 (12), p.1253-1255
Hauptverfasser:	André, Virginie, Vidal, Anne, Ollivier, Jean, Robin, Sylvie, Aitken, David J.
Format:	Artikel
Sprache:	eng
Schlagworte:	[2+2] Cycloaddition Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Amino acids Chemistry Cycloaddition Cyclobutanes Ethylene Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Photochemical Photochemical synthesis Photochemistry Physical chemistry of induced reactions (with radiations, particles and ultrasonics) Preparations and properties Pyrrolinones Strategy Tetrahedrons Unsaturated γ-Amino acids
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Beschreibung
Zusammenfassung:	The (+)-(1 R,2 S) and (−)-(1 S,2 R) stereoisomers of 2-(aminomethyl)cyclobutane-1-carboxylic acid have been prepared using a short and efficient strategy, which employs the photochemical [2+2] cycloaddition reaction between ethylene and an unsaturated γ-lactam as the key step.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2011.01.013