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Modified Guanidines as Potential Chiral Superbases. 2. Preparation Of 1,3-unsubstituted and 1-substituted 2-iminoimidazolidine Derivatives and a Related Guanidine by the 2-chloro-1, 3-dimethylimidazolinium Chloride-Induced Cyclization of Thioureas

Modified Guanidines as Potential Chiral Superbases. 2. Preparation Of 1,3-unsubstituted and 1-substituted 2-iminoimidazolidine Derivatives and a Related Guanidine by the 2-chloro-1, 3-dimethylimidazolinium Chloride-Induced Cyclization of Thioureas

T Isobe, K Fukuda, T Tokunaga, H Seki, K Yamaguchi, T Ishikawa

J Org Chem. 2000 Nov 17;65(23):7774-8.

PMID: 11073580

Abstract:

Simple preparation methods for modified guanidines were explored for new chiral superbases. Thus, (4S,5S)-4,5-diphenyl- and diastereomeric cyclohexane-fused 2-iminoimidazolidines were prepared from (1S,2S)-1,2-diphenylethylenediamine and (1R,2R)- or (1S,2S)-1, 2-diaminocyclohexanes through cyclization of protected thiourea intermediates with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a key reaction. In the (4S,5S)-4,5-diphenyl series 1-methyl-2-iminoimidazolidines and 2-diethylaminoimidazoline were also prepared as related guanidines.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP29841698	(1S,2S)-(−)-1,2-Diphenylethylenediamine		29841-69-8	Price

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