• Bulletin of the Korean Chemical Society
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• 제31권10호
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• pp.2776-2782
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• 2010

Newly developed Horner-Wadsworth-Emmons (HWE) reagents 5 having triphenylphosphorane ylide subunits readily condensed with various carbonyl compounds under mild reaction conditions to afford $\beta,\gamma$-unsaturated $\alpha$-keto triphenylphorane ylides in good to excellent yields, which were hydrogenated over Pd-C (10%)/$H_2$ (1 atm) to give the corresponding $\alpha$-keto triphenylphorane ylides in quasi-quantitative yields. These triphenyphosphorane ylides have been utilized as the precursors to $\alpha$-keto amide/ester and vicinal tricarbonyl units in Wasserman's synthetic protocols, and have previously been prepared only from carboxylic acids/acid chlorides. Our new approaches provide excellent alternatives for the synthesis of triphenylphosphorane ylide precursors to $\alpha$-keto amide/ester and vicinal tricarbonyl units directly from carbonyl compounds in good to excellent yields.

• Bulletin of the Korean Chemical Society
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• 제28권10호
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• pp.1641-1642
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• 2007

• Bulletin of the Korean Chemical Society
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• 제30권11호
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• pp.2521-2522
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• 2009

• Bulletin of the Korean Chemical Society
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• 제34권12호
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• pp.3545-3546
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• 2013

• Bulletin of the Korean Chemical Society
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• 제34권10호
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• pp.2953-2958
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• 2013

A noble phenylsulfonyl reagent 8 having ${\alpha}$-oxo (cyanomethylene)triphenylphosphorane ylide subunit readily condensed with various alkyl halides under basic conditions to afford ${\beta}$-alkyl-${\alpha}$-oxo-${\beta}$-phenylsulfonyl (cyanomethylene)triphenylphosphorane ylides 9 in excellent yields. These sulfonyl ylides 9 were then reductively desulfonylated with $Na(Hg)/Na_2HPO_4$ in the presence of methanol to provide ${\alpha}$-keto (cyanomethylene)-triphenylphosphorane ylides 2' in good to excellent yields. Our new synthetic approach offers an expeditious access to various ${\alpha}$-keto (cyanomethylene)triphenylphosphorane ylides from alkyl halides utilizing a new phenylsulfonyl reagent as the key reagent under mild reaction conditions in good overall yields.

• Bulletin of the Korean Chemical Society
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• 제23권2호
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• pp.351-354
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• 2002

A number of bis-2-oxo amide triacylglycerol analogues, a recently reported potent human gastric lipase inhibitor and its new analogues, have been prepared starting from 1,3-dibromo-2-propanol utilizing acyl cyanophosphorane methodology as a key step in a convergent manner. The key coupling reaction has been accomplished at -$78^{\circ}C$ between 1,3-diamino-2-propanol derivative and the labile diketo nitriles, derived from acyl cyanotriphenylphosphoranes upon oxidizing with $O_3$, under mild condition in moderate yields.

• 대한화학회지
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• 제48권2호
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• pp.161-170
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• 2004

일련의 유효한 ${\gamma}$-아미노부틸산에서 유도된 인간 시토솔릭 포스포리파제 A$_2$ 저해제를 아실 시아노포스포레인과 아민 유도체로 부터 수렴적으로 합성하였다. 저해제 내의 친전자적인 단편인 알파-케토 아미드 작용기는 불안정한 ${\alpha},{\beta}$-디케토 니트릴과 ${\gamma}$-아미노부틸산 삼차-부틸에스테르 유도체와의 직접 융합반응에 의하여 -78 $^{\circ}C$에서 양호한 수율로 합성하였다.