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Nucleophilic ring opening of tetrahydro-1,3-oxazines and 1,3-oxazolidines by alkynyl anions: A novel synthesis of β-aminoacetylenes

✍ Scribed by Ming-Jung Wu; Der-Shenq Yan; Hui-Wen Tsai; Shu-Hui Chen

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 202 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)73304-1

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✦ Synopsis

The ring opening of tetrabydro-1 ,Zoxazines by nucleophilic agents, such as lithium aluminum hydride,' and bmmozincio a~&@,~ provided a useful synthetic method to fonn faminopmpanol derivatives. In our currem development of the enantioselective synthesis of (+)-rnemquinine (l), the ~p~l~nop~p~ol2 appeared to be an at&active synthetic interm&iate for the ~~ of (+~~u~. ~~~ 2 could be formed by direct ring opening of Id-oxazinane 3 with metal acetylides 4 (R' = CHzSiMe& This thought has stimulated us to invest&ate these ring opening reactions. ,CQH =3 "N-OH

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