SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF CAMPHANATES OF (-)-(2S,3S)-4-PHENYL-3-BROMO-2-BUTANOL AND (-(2S,3R)-4-PHENYL-3-BROMO-2-BUTANOLDIASTEREOISOMERS())

The X-ray crystal structures of (-)-syn-4-phenyl-3-bromo-2-butyl camph anate (I) and (+)-anti-4-phenyl-3-bromo-2-butyl camphanate (II) have b een determined. The syn diastereoisomer of bromohydrin has the (2S,3S) absolute configuration whereas the anti diastereoisomer has the (2S,3 R) absolute configuration. The crystallized derivatives I and II have been obtained by the reaction of each stereoisomer of bromohydrin, syn thesized by reduction with baker's yeast, with (1S)-camphanic chloride . Crystal data: (I) C20H25BrO4:M(W):409.32; orthorhombic, P2(1)2(1)2(1 ); a = 11.245(3), b = 12.086(1), c = 14.512(4) Angstrom; Z = 4; final R = 0.053 for 1819 observed reflections. (II) C20H25BrO4; M(W) = 409.3 2; monoclinic, P2(1); a = 11.352(1), b = 6.378(1), c = 14.255(2) Angst rom, beta = 110.38(1)degrees; Z = 2; final R = 0.045 for 1672 observed reflections.