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Synlett 2001; 2001(12): 1950-1952
DOI: 10.1055/s-2001-18778
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2,3-Dihydro-4H-1,3-oxazin-4-ones, Novel Auxiliaries for the Stereoselective Synthesis of 1β-methylcarbapenems

Do K. Pyun* , Won J. Jeong, Hee J. Jung, Jae H. Kim, Jin S. Lee, Cheol H. Lee, Bong J. Kim
  • *Korea Research Institute of Chemical Technology, PO Box 107, Yusung, Taejon 305-600, Korea; Fax: + 82(42)8611291; E-mail: bjkim@pado.krict.re.kr
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Publication Date:
04 December 2001 (online)

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Dihydrooxazinones 9, prepared from benzylcyanide in two steps serve as efficient auxiliaries for the stereoselective synthesis of β-methylcarbapenem intermediate 2. Reformatsky-type reactions of 4-acetoxyazetidinone with α-bromopropionyl dihydrooxazinone 10 provided β-methylazetidinones 4 in high diastereoselectivities. The auxiliaries 9 were also easily removed in the Dieckmann cyclization leading to β-methylcarbapenem skeletons. Practical synthesis of β-methylenolphosphates 2 from 4-acetoxyazetidinone 3 was achieved in three steps (61-77% overall yield).

auxiliary - diastereoselective - β-methylcarbapenem - Reformatsky-type reaction - Dieckmann cyclization