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Asymmetric synthesis of axially chiral 1-(2′-methyl-3′-indenyl)naphthalenes via prototropic rearrangements of stable rotamers of 1-(2′-methyl-1′-indenyl)naphthalenes

✍ Scribed by Robert W. Baker; Joost N.H. Reek; Brian J. Wallace

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 280 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01369-0

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✦ Synopsis

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 °C leads to the formation of an 18:1 mixture of -ac:+sc-6 rotamers, with a barrier to atropisomerisation of AG:[:353 = 28.4 kcal mol d (+sc to-ac). Prototropic rearrangements of the rotamers of l-(2'-methyl-l'indenyl)naphthalenes to 1-(2'-methyl-3'-indenyl)naphthalenes occur with retention of the axial stereogenic element.

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