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  • Catalytic asymmetric construction of spiro(γ-butyrolactam-γ-butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides.

Catalytic asymmetric construction of spiro(γ-butyrolactam-γ-butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides.

Chemistry (Weinheim an der Bergstrasse, Germany) (2012-08-29)
Huai-Long Teng, He Huang, Chun-Jiang Wang
RÉSUMÉ

Spiro(γ-butyrolactam-γ-butyrolactone): a route to enantioenriched spiro(γ-butyrolactam-γ-butyrolactone) compounds, a valuable motif for drug discovery, was developed by use of a highly efficient copper(I)/TF-BiphamPhos-catalyzed tandem Michael addition-elimination of homoserine lactone derived cyclic imino esters with Morita-Baylis-Hillman (MBH) bromides, followed by treatment with para-toluenesulfonic acid.

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Description du produit

Sigma-Aldrich
p-Toluenesulfonic acid monohydrate, ACS reagent, ≥98.5%
Sigma-Aldrich
Sodium p-toluenesulfonate, 95%
Sigma-Aldrich
p-Toluenesulfonic acid monohydrate, ReagentPlus®, ≥98%
Sigma-Aldrich
Silver p-toluenesulfonate, ≥99%
Sigma-Aldrich
(S)-α-Amino-γ-butyrolactone hydrochloride, 97%
Sigma-Aldrich
α-Amino-γ-butyrolactone hydrobromide, 99%
Sigma-Aldrich
Dihydro-3-amino-2-(3H)-furanone, AldrichCPR