Mekala, Shekar published the artcileA Scalable, Nonenzymatic Synthesis of Highly Stereopure Difunctional C4 Secondary Methyl Linchpin Synthons, Synthetic Route of 21286-54-4, the publication is Journal of Organic Chemistry (2015), 80(3), 1610-1617, database is CAplus and MEDLINE.
In response to the continuing widespread use of heterodifunctional C4 secondary Me building blocks in asym. synthesis, we have developed a mole-scale, two-step synthesis of a 1:1 mixture of the diastereomers of 3-bromo-2-methyl-1-Pr camphorsulfonate (casylate). One isomer I has been crystallized to >99:1 dr in â?5% yield. Equilibration of the mother liquor (enriched in the other isomer) to a 1:1 mixture and recrystallization significantly raises the overall yield of I. Applications of I include chemoselective Grignard coupling, enabling the very short synthesis of highly stereopure long-chain natural products containing remote, methyl-bearing stereogenic centers [e.g., (R)-tuberculostearic acid (II)], with complete control of configuration. Also, Ag-mediated, completely chemoselective Br displacement from I leads to a range of >99:1 er difunctional synthons. Both applications incorporate concurrent recovery of CasO. The enantiomer of I can be made from com. (1R)-10-CasOH.
Journal of Organic Chemistry published new progress about 21286-54-4. 21286-54-4 belongs to chlorides-buliding-blocks, auxiliary class Chiral,Chloride,Sulfonyl chlorides,Aliphatic cyclic hydrocarbon,Ketone, name is ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, and the molecular formula is C10H15ClO3S, Synthetic Route of 21286-54-4.
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