881099-31-6Relevant articles and documents
A Stereoselective aza-Prins Reaction: Rapid Access to Enantiopure Piperidines and Pipecolic Acids
Mittapalli, Ramana Reddy,Coles, Simon J.,Klooster, Wim T.,Dobbs, Adrian P.
, p. 2076 - 2089 (2021/02/03)
The aza-Prins reaction is a widely employed and highly efficient method for the preparation of saturated nitrogen-containing heterocycles. Its major drawback has always been a lack of diastereoselectivity and the formation of racemic products. Herein, we address these problems and report, for the first time, the synthesis of both diastereomerically and enantiopure multiply substituted piperidines via the aza-Prins reaction. This method is widely applicable for natural product synthesis and is exemplified here by the synthesis of enantiopure pipecolic acid derivatives.
Diastereoselective allylstannane additions to (S)-5,6-dihydro-2H-5- phenyloxazin-2-one. A concise synthesis of (S)-β-methylisoleucine
Pigza, Julie A.,Molinski, Tadeusz F.
scheme or table, p. 1256 - 1259 (2010/05/18)
Chemical Equation Presented The addition of allyl stannanes to (S)-4,5-dihydro-5-phenyl-2H-oxazinone (3) was achieved under Bronsted acid catalysis to give 2-allylmorpholinones with high diastereoselectivity (up to dr 14.2:1). The product of dimethylallyltributylstannane addition to 3 was converted to L-β-methylisoleucine, an α-amino acid residue found In the complex, biologically active marine-derived peptides polytheonamides A and B, and polydiscamides A-C.
New utilizations of optically active homoallylamines: Highly stereoselective synthesis of cyclic guanidine and thiourea
Yanada, Reiko,Kaieda, Akira,Yanada, Kazuo,Takemoto, Yoshiji
, p. 101 - 106 (2007/10/03)
Halocyclizations of optically active homoallylguanidine and homoallylthiourea were examined. These reactions proceeded stereoselectively to give six membered cyclic guanidines and thiourea. High 1,3-asymmetric induction by the homoallylic substituents is
