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Total synthesis of methyl l-daunosaminide hydrochloride via chiral 1,3-oxazine

โœ Scribed by Jin, Tian; Kim, Jin-Seok; Mu, Yu; Park, Seok-Hwi; Jin, Xiangdan; Kang, Jong-Cheol; Oh, Chang-Young; Ham, Won-Hun


Book ID
121771657
Publisher
Elsevier Science
Year
2014
Tongue
French
Weight
604 KB
Volume
70
Category
Article
ISSN
0040-4020

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Asymmetric synthesis of axially chiral 1
โœ Robert W. Baker; Joost N.H. Reek; Brian J. Wallace ๐Ÿ“‚ Article ๐Ÿ“… 1998 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 280 KB

Reaction of methyl (R)-l-(p-tolylsulfinyl)naphthalene-2-carboxylate 2 with 2-methylindenyllithium affords the -ac rotamer of methyl (S)-l-(2'-methyl-l'-indenyl)naphthalene-2-carboxylate 6 in 63% ee. Heating -ac-6 at 80 ยฐC leads to the formation of an 18:1 mixture of -ac:+sc-6 rotamers, with a barrie