• Bulletin of the Korean Chemical Society
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• v.28 no.4
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• pp.629-634
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• 2007

Photochemical reactions of N-methylphthalimide with silyl enol ethers have been explored. Irradiations of phthalimide (1) and cyclic silyl enol ethers (5a-b) are observed to promote formation of photoreduced phthalimides and photoaddition products by sequential SET-desilylation pathways. The photoreaction of phthalimide (1) and acyclic silyl enol ethers (5c-d) leads to produce oxetanes which arise by competitive single electron transfer (SET) and classical 2+2 photocycloaddition (Parteno-Buchi reaction) pathways.

• Bulletin of the Korean Chemical Society
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• v.15 no.5
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• pp.337-338
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• 1994

• Bulletin of the Korean Chemical Society
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• v.32 no.spc8
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• pp.2887-2888
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• 2011

• Bulletin of the Korean Chemical Society
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• v.32 no.10
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• pp.3738-3742
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• 2011

Bismuth tribromide ($BiBr_3$) 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 $BiBr_3$, 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 ${\beta}$-amino ketones and N-Cbz-protected ${\beta}$-amino esters in moderate to good yield, respectively.

• Bulletin of the Korean Chemical Society
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• v.17 no.2
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• pp.153-158
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• 1996

The synthesis of common skeleton of podosporin A and aureol was studied through cationic olefin cyclization as a key step. The generation of thermodynamic silyl enol ether or enol acetate under known conditions gave regioselectivity of 88:12. The enolate alkylation of 2,3-dimethylcyclohexanone with 2,5-dimethoxybenzyl bromide at the more substituted site via lithium enolate gave poor yield. In this case an organozincate or an ammonium enolate also proved to be ineffective or not practical in terms of yield. Side chain elongation of the substituted cyclohexanone 13 through Grignard reaction, Wittig reaction, or Shappiro reaction did not proceed because of steric hindrance and side reactions. However, Stille coupling reaction via enol triflate produced the desired product 18 in high yield. The advanced intermediate 22, which was efficiently synthesized from 18, produced 24 instead of the desired product under a cationic olefin cyclization condition, indicating that the cyclization occurred in a stepwise mannervia the organomercury intermediate 23.

• Bulletin of the Korean Chemical Society
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• v.23 no.1
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• pp.86-92
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• 2002

A short synthesis of novel prostanoids, 12-epi-carbacyclins 3 and 24, has been accomplished using palladium chemistry as a key step. The silyl enol ether 10a prepared through organopalladium chemistry has been allowed to react with 1-octen-3-one in the presence of $Pd(OAc)_2$ to give compound 12 in a single step. The unusual chemo- and stereoselective reduction of the ${\alpha},{\beta}$-unsaturated ketone in 12 has been effected with (S)-BINALH. Subsequent desilylation and Wittig reaction have provided the Subsequent desilylation and Wittig reaction have provided the $PGI_2$ analogues 3 and 24.