Acta Crystallographica Section C

Crystal Structure Communications

Volume 57, Part 12 (December 2001)

Acta Cryst. (2001). C57, 1415-1417 [doi:10.1107/S0108270101014597]

Full stereochemical understanding in a new (2R,3R,4R)-4-hydroxyisoleucine synthesis

M. Rolland, T. Kassem, V. Rolland and J. Martinez

Abstract: We present the crystal and molecular structures of 2,3,6,7,8,8a-hexahydro-6,8-methano-7,7,8a-trimethyl-3-(1-methyl-2-oxopropylidene)-5H-1,4-benzoxazin-2-one, C₁₆H₂₁NO₃, (III), and 2,3,6,7,8,8a-hexahydro-3-(2-hydroxy-1-methylpropyl)-6,8-methano-7,7,8a-trimethyl-5H-1,4-benzoxazin-2-one, C₁₆H₂₅NO₃, (V). These compounds are two of the four key intermediates in our synthetic route to (2R,3R,4R)-4-hydroxyisoleucine. The two structures provide a full understanding of the stereochemistry in successive steps. This synthesis was based on a new optically pure chiral oxazinone auxiliary derived from (1R,2R,5R)-2-hydroxypinan-3-one.

Formula: C₁₆H₂₁NO₃ and C₁₆H₂₅NO₃

Online 6 December 2001


	Structure factor file (CIF format) (70.6 kbytes) Contains datablock III

	Structure factor file (CIF format) (70.6 kbytes) Contains datablock V

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