NDLI: Approach to synthesis of novel chiral 3-chloro-2(5H)-furanone and its application in asymmetric reactions

Content Provider	Springer Nature Link
Author	Huang, Hui Chen, Qinghua
Copyright Year	2000
Abstract	The synthetic method of the novel chiral synthon, 5-l-menthyloxy-3-chloro-2-(5H)-furanone 5a and its application in asymmetric reactions were investigated. 5a is easily obtained in highly optical purity, and acts as a stable acceptor of Michael addition with oxygen nucleophiles in tandem double Michael addition / internal nucleophilic substitution to offer the spiro-cyclopropane derivative containing four stereogenic centers 8, which it is difficult to obtain by routine methods. The synthetic methods for 5a and 8 are reported in detail and the new compounds are identified on the basis of their analytical data and spectroscopic data, such as UV, IR,$^{1}$H NMR,$^{13}$C NMR, MS and elementary analysis. The absolute configuration of the interesting spiro-cyclopropanes, spiro [1-chloro-4-(l-menthyloxy)-5-oxo-6-oxa-biscyclo[3.1.0]hexane-2,3′-(4′-/-menthyloxy-5′-l-menthyloxybutyrolactone)] 8 was established by X-ray crystallography. This result can provide important synthetic strategy in synthesis of some complex molecules containing spiro-cyclopropane skeleton with multiple chiral centers.
Starting Page	711
Ending Page	716
Page Count	6
File Format	PDF
ISSN	10016538
Journal	Chinese Science Bulletin
Volume Number	45
Issue Number	8
e-ISSN	18619541
Language	English
Publisher	Science in China Press
Publisher Date	2000-01-01
Publisher Place	Beijing
Access Restriction	Subscribed
Subject Keyword	new chiral synthon 5-l-menthyloxy-3-chloro-2-(5H)-furanone absolute configuration spiro-cyclopropane derivative containing multiple chiral centers Life Sciences Physics Chemistry/Food Science Science Geosciences Engineering
Content Type	Text
Resource Type	Article
Subject	Multidisciplinary

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Synthesis of spiro-cyclopropane derivatives containing multiple chiral centers

Asymmetric synthesis of β-lactams via amine additions to 5(R)-menthyloxy-2[5H]-furanone.

Application of modified amino acid as a chiral building block in asymmetric synthesis

(S)-5-(l-Menthyloxy)-5-[(2R,3R)-2-(l-menthyloxy)-5-oxotetrahydrofuran-3-yl]furan-2(5H)-one

An Efficient Synthesis of 2(5H)-Furanone and Furan Derivatives Using 3-(Phenylthio)propenal as a 1, 3-Dipolar Synthon

Summary: the intermolecular diels alder reactions of 5-menthyloxy-2[5h]-.

Microflow Photochemistry - Acetone sensitized Addition of Isopropanol to (5R)-5-Menthyloxy-2-(5H)-furanone

Solid-Phase Microextraction for Determination of 3-Chloro-4-(dichloromethyl)- 5-hydroxy-2[5H]-furanone in Water

Temporary Changes in the dc ElectricalConductivity of MX (3-Chloro-4(Dichloromethyl)-5-Hydroxy-2(5H)-Furanone) Treated Collagen.

Approach to synthesis of novel chiral 3-chloro-2(5H)-furanone and its application in asymmetric reactions

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