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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 10
BKCSDE 32(10)
October 20, 2011 

Mannich-type Reactions of in Situ Generated N-Acyliminium Ions from α-Amido p-Tolylsulfones with Silyl Enolates
Sang-Hyeup Lee *Santosh T. Kadam *
α-Amido p-tolylsulfone, Cbz-Protected β-amino ketone, N-Acyliminium ion, Mannich-type reaction
Bismuth tribromide (BiBr3) catalyzed Mannich-type reactions of N-acyliminium ions which generated in situ from N-benzyloxycarbonylamino p-tolylsulfones have been developed. In the presence of catalytic amount of BiBr3, N-benzyloxycarbonylamino p-tolylsulfones prepared from aromatic and aliphatic aldehydes reacted with silyl enol ether and silyl enol ester under mild reaction conditions to afford N-Cbz-protected β-amino ketones and N-Cbz-protected β-amino esters in moderate to good yield, respectively.
3738 - 3742
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