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Stereoselective Polymer-Supported Synthesis of Morpholine- And Thiomorpholine-3-carboxylic Acid Derivatives

Stereoselective Polymer-Supported Synthesis of Morpholine- And Thiomorpholine-3-carboxylic Acid Derivatives

Petra Králová, Veronika Fülöpová, Michal Maloň, Tereza Volná, Igor Popa, Miroslav Soural

ACS Comb Sci. 2017 Mar 13;19(3):173-180.

PMID: 28085245

Abstract:

Herein we report the polymer-supported synthesis of 3,4-dihydro-2H-1,4-oxazine-3-carboxylic acid derivatives using immobilized Fmoc-Ser(tBu)-OH and Fmoc-Thr(tBu)-OH as the starting materials. After the solid-phase-synthesis of N-alkyl-N-sulfonyl/acyl intermediates, the target dihydrooxazines were obtained using trifluoroacetic acid-mediated cleavage from the resin. This approach was also studied for the preparation of dihydrothiazines from immobilized Fmoc-Cys(Trt)-OH. Inclusion of triethylsilane in the cleavage cocktail resulted in the stereoselective formation of the corresponding morpholine/thiomorpholine-3-carboxylic acids. Stereochemical studies revealed the specific configuration of the newly formed stereocenter and also the formation of stable N-acylmorpholine rotamers.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
IAR42410620	Fmoc-Ser(tBu)-OH-15N			Price

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