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200517.fm Page 51 Friday, March 18, 2005 2:52 PM
2005
Reduction
O 0220
17- 049
Unusual Migrations and Cyclization in the Preparation of β-Azido Alcohols from
β-Hydroxy Esters. — The migration of Tbs and Boc groups from secondary to primary alcohols during the reduction of the β-esters (I) and (III), respectively, is observed.
Also, unusual cyclization occurs during the tosylation of the benzylic alcohol (V) in the
presence of NEt3 and DMAP to give the carbonate (VII). For this reaction a possible
mechanism including a SN2 inversion is discussed. — (MADHUSUDHAN*, G.;
REDDY, G. O.; RAMANATHAM, J.; DUBEY, P. K.; Indian J. Chem., Sect. B: Org.
Chem. Incl. Med. Chem. 43 (2004) 12, 2719-2723; Technol. Dev. Cent., Dr. Reddy's
Lab. Ltd., Hyderabad 500 050, India; Eng.) — H. Haber
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