Synthesis of Enantiopure Mixed Alkyl-Aryl Vicinal Diamines by the Diaza-Cope Rearrangement: A Synthesis of (+)-CP-99,994

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The stereoselective synthesis of mixed alkyl-aryl vicinal diamines was demonstrated by the use of 1,2-bis(2-hydroxyphenyl)-1,2-diaminoethene (hpen). A sequential addition of aryl and alkyl aldehyde to hpen gave a fused imidazolidinedihydro-1,3-oxazine ring stereoselectively, which undergoes the diaza-Cope rearrangement to provide mixed vicinal diimines at elevated temperature in good yields and excellent stereoselectivity. We also showed that (+)-CP-99,994 can be readily prepared by the diaza-Cope rearrangement in overall 42% yield.
Publisher
AMER CHEMICAL SOC
Issue Date
2017-12
Language
English
Article Type
Article
Keywords

TERT-BUTANESULFINYL IMINES; AZA-HENRY REACTION; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOSPECIFIC SYNTHESIS; ENANTIOMERICALLY PURE; CONJUGATED DIENES; CHIRAL DIAMINES; MOTHER DIAMINE; (+)-L-733,060

Citation

JOURNAL OF ORGANIC CHEMISTRY, v.82, no.23, pp.12050 - 12058

ISSN
0022-3263
DOI
10.1021/acs.joc.7b01751
URI
http://hdl.handle.net/10203/237683
Appears in Collection
CH-Journal Papers(저널논문)
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