72856-35-0Relevant articles and documents
Highly diastereoselective cycloaddition reactions of variously substituted 1-thia- and 1-thia-3-aza-buta-1,3-dienes. Synthesis of enantiomerically pure 5,6-dihydro-4H-[1,3]thiazines and 3,4-dihydro-2H-thiopyrans
Harrison-Marchand, Anne,Collet, Sylvain,Guingant, André,Pradère, Jean-Paul,Toupet, Lo?c
, p. 1827 - 1839 (2007/10/03)
The cycloaddition of 2- or 2,3-substituted 1-thia- and 1-thia-3-aza-4- dimethylamino-buta-1,3-dienes with various dienophiles in the presence of a Lewis acid provides a rapid and diastereoselective access to the 3,4-dihydro-2H-thiopyran and 5,6-dihydro-4H-[1,3]thiazine backbones. The generally observed trans relationship between the two newly created strereogenic centres was demonstrated to be the expression of a thermodynamic control of the reaction. The use of chiral dienophile derived from chiral oxazolidin-2-ones allowed us to prepare enantiopure 5,6-dihydro-4H-[1,3] thiazines and 3,4-dihydro-2H-thiopyrans. In the asymmetric synthetic process the chiral auxiliary removal step was best accomplished in the presence of samarium triflate in methanol.
Diels-Alder and Retro-Diels-Alder Reactions: From N'-(Thioacyl)formamidines to Thio Amide Vinylogues
Gokou, Celestin Tea,Pradere, Jean-Paul,Quiniou, Herve
, p. 1545 - 1547 (2007/10/02)
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