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

DOI: 10.1016/S0040-4039(98)01369-0

Source and publish data:

Tetrahedron Letters p. 6573 - 6576 (1998)

Update date:2022-08-04

Topics:

Authors:

Baker, Robert W.

Reek, Joost N.H.

Wallace, Brian J.

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Article abstract of DOI:10.1016/S0040-4039(98)01369-0

Reaction of methyl (R)-1-(p-tolylsulfinyl)naphthalene-2-carboxylate 2 with 2-methylindenyllithium affords the -ac rotamer of methyl (S)-1-(2'- methyl-1'-indenyl)naphthalene-2-carboxylate 6 in 63% ee. Heating -ac-6 at 80 °C leads to the formation of an 18:

Full text of DOI:10.1016/S0040-4039(98)01369-0

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