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Attempted SN2 OH → Cl substitution. Representative reactions tested include: (1) CCl4, PPh3, CH2Cl2, rt; 93% ee → 50% ee, (2) Cl3CCONH2, PPh3, CH2Cl2, rt; 93% ee → 70% ee, and (3) a. MsCl, Et3N, CH2Cl2, rt and b. LiCl, DMF, rt; 93% ee → 75% ee.
