Diastereoselective Ring-Opening Aldol-Type Reaction of 2,2-Dialkoxycyclopropanecarboxylic Esters with Carbonyl Compounds. 1. Synthesis of Cis 3,4-Substituted γ-Lactones

DOI: 10.1021/jo00052a028

Source and publish data:

Journal of Organic Chemistry p. 7126 - 7133 (1992)

Update date:2022-08-04

Topics: Synthesis Oxidation IR spectroscopy Asymmetric synthesis Enantiomer Regioisomer Regioselectivity Lewis acid Yield NMR spectroscopy Catalyst Strecker synthesis Equilibrium Mass spectrometry Selectivity Hydrogenation Nucleophile Electrophile Heck reaction Solvent reflux Stereochemistry Reduction Enantioselectivity Steric hindrance Enantiomeric excess (ee) Deprotonation Rearrangement Chromatography Recrystallization Hydrolysis Esterification Baylis-Hillman reaction Nucleophilic substitution Cross-coupling Mitsunobu reaction Dipolarophile Kinetics Conformation Radical Diastereoselective Michael reaction Conjugate addition Bischler-Napieralski reaction Ullmann reaction TLC (thin-layer chromatography) Proton transfer Dehydrogenation Protecting group Lossen rearrangement

Authors:

Shimada, Shigeru

Hashimoto, Yukihiko

Sudo, Atsushi

Hasegawa, Masaki

Saigo, Kazuhiko

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Article abstract of DOI:10.1021/jo00052a028

The Lewis-acid promoted reactions of 2,2-dialkoxycyclopropanecarboxylic esters 4a-c with aldehydes and unsymmetrical ketones to give γ-lactones were investigated.TiBr4 is an excellent catalyst and gives cis 3,4-substituted γ-lactones in good yields with h

Full text of DOI:10.1021/jo00052a028

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