Stereoselective Synthesis and Study on the Stereochemistry of trans-2-Substituted-thiosemicarbazido-4-aryl-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinanes

Chem. J. Chinese Universities

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Stereoselective Synthesis and Study on the Stereochemistry of trans-2-Substituted-thiosemicarbazido-4-aryl-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinanes

FENG De-Xin, CHEN Ru-Yu, HUANG You

National Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

Received:2005-12-19 Revised:1900-01-01 Online:2006-12-10 Published:2006-12-10
Contact: CHEN Ru-Yu

Abstract

Abstract: 1,3,2-Dioxaphosphorinane derivatives are an important class of organophosphorus heterocycles, which continue to attract considerable interest due to their unique stereochemical features and diverse potential biological importance. It has been found that the stereochemistry is important for the bioactivities of 1,3,2-dioxaphosphorinane compounds. Therefore, there is still a need for the development of a more simple and convenient method for the stereoselective synthesis of 1,3,2-dioxaphosphorinane derivatives. In this article, novel trans-2-substituted-thiosemicarbazido-4-aryl-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinanes 5a—5j were synthesized via a series of reactions such as aldol-Cannizzaro, cyclization and addition and their structures are characterized by elemental analysis, ¹H NMR, ¹³C NMR and ³¹P NMR. Their epimers at the phosphorus atom were found by the isomerization in DMSO-d₆. This study gave a good explanation for the correlation between the configurational assignments and the chemical shifts of C4—H and ³¹P NMR.

Key words: 1,3,2-Dioxaphosphorinane, Thiosemicarbazide, Isomerization

CLC Number:

O626

TrendMD:

FENG De-Xin, CHEN Ru-Yu, HUANG You. Stereoselective Synthesis and Study on the Stereochemistry of trans-2-Substituted-thiosemicarbazido-4-aryl-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinanes[J]. Chem. J. Chinese Universities, doi: .

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Stereoselective Synthesis and Study on the Stereochemistry of trans-2-Substituted-thiosemicarbazido-4-aryl-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinanes

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