Journal
ORGANIC LETTERS
Volume 17, Issue 19, Pages 4746-4749Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02268
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Funding
- Basic Science Research Program through National Research Foundation of Korea (NRF) - Ministry of Education [NRF-2013R1A1A2059838]
- Ministry of Science, ICT & Future Planning [NRF-2013R1A1A2073207]
- National Research Council of Science and Technology [Creative Allied Project (CAP)]
- Korea Basic Science Institute [C35705]
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A convenient one-pot procedure to synthesize a variety of highly optically active syn-alpha-aryl-beta-hydroxy Weinreb amides using an asymmetric Roskamp/reduction strategy is described. An oxazaborolidinium ion catalyzed asymmetric Roskamp reaction of alpha-aryl diazo Weinreb amides with aldehydes produced alpha-phenyl-beta-keto Weinreb amides, which were in situ reduced with zinc borohydride to give syn-alpha-aryl-beta-hydroxy Weinreb amides in good yields (up to 87%) with high enantioselectivities (up to 99% cc) and syn stereoselectivities (>20:1).
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