Synlett 2001; 2001(12): 1950-1952
DOI: 10.1055/s-2001-18778
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
04 December 2001 (online)

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).