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(from (S)-22). [a]D20 2.66 (c 0.67, CHCl3). 1H-NMR: 7.34 7.18 (m, 5 arom. H); 4.32( quint. d, J 5.9, 9.5,
HÀC(2)); 4.02 (d, J 8.2, 1 HÀC(5)); 3.90 (d, J 8.2, 1 HÀC(5)); 2.22 (dd, J 12.1, 5.9, 1 HÀC(3)); 1.85 (dd,
J 12.1, 9.5, 1 HÀC(3)); 1.43 (s, MeÀC(4)); 1.29 (d, J 5.9, MeÀC(2)). 13C-NMR: 147.8; 128.3; 126.0; 125.9;
125.7; 78.5; 74.9; 47.9; 28.1; 21.4. GC/MS: 176 (12, M ); 146 (23), 131 (100).
7.2.4. (2R,4S)-Tetrahydro-2,4-dimethyl-4-phenylfuran ((2R,4S)-3). According to GP3, with (2S,4S)-27
(1.1 g, 4.7 mol): (2R,4S)-3 (0.401 g, 49%). Chemical purity 97% by GC/MS (tR 13.78); 78% de; > 99% ee (from
(R)-23). [a]2D0 À39.5 (c 0.4, CHCl3). 1H-NMR and GC/MS: in accordance with those of the enantiomer.
7.2.5. (2S,4S)-Tetrahydro-2,4-dimethyl-4-phenylfuran ((2S,4S)-3). NBS (1.19 g, 6.69 mmol) was added to a
soln. of (2S,4S)-26 (1.0 g, 5.15 mmol) and PPh3 (1.75 g, 6.69 mmol) in CH2Cl2 (20 ml). After 30 min at r.t., the
mixture was poured into H2O and extracted with CH2Cl2. The org. phase was dried (Na2SO4) and evaporated
and the residue submitted to CC (hexane): (2S,4S)-3 (0.607 g, 67%); 60% de, > 99% ee. [a]2D0 À 10.2( c
1
0.84, CHCl3). H-NMR and GC/MS: in accordance with those of the enantiomer.
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