• Journal of Photoscience
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• 제12권2호
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• pp.63-66
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• 2005

The azomethine ylide forming photoreaction has been explored by probing the excited state chemistry of several N-trimethylsilylmethyl substituted cyclic and acyclic imides and amide analogs. N-[(Trimethylsilyl)methyl]-N-mesylbenzamide (5) undergoes the excited state C to O silyl migration reaction to produce azomethine ylide intermediate 13. This ylide undergoes electrocyclization to form transient aziridine intermediate 14 which react further by ring opening to generate N-phenacylamine product 10. On the other hand, photolysis of N-[N-mesyl-N-(trimethylsilyl)methyl]aminoethyl-N-mesylbenzamide (8) brings about desilylation resulting in the production of dimer 17.

• Bulletin of the Korean Chemical Society
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• 제33권7호
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• pp.2213-2218
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• 2012

Efficient synthetic routes were developed to prepare a sizable amount (4-15 grams) of the chiral epoxides 4-6 as versatile intermediates for the synthesis of aspartyl protease inhibitors of therapeutic interest such as HIV protease and ${\beta}$-secretase. Oxidative cleavage of the C(2)-C(3) double bond of L-ascorbic acid followed by functional group manipulation led to the preparation of the epoxide 10, which was opened with an azide to yield a common aziridine intermediate 12. Through opening of the aziridine ring of 12 with either a carbon or a sulfur nucleophile, chiral epoxide precursors 4-6 could be prepared for various HIV protease inhibitors. Except for the final low melting epoxides 5 and 6, all intermediates were obtained as crystalline solids, thus the synthetic pathway can be easily applied to a large-scale synthesis of the chiral epoxides.

• 대한화학회지
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• 제13권3호
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• pp.229-232
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• 1969

2,2-gem-dephenylaziridine의 醋酸에 의한 開環反應에서 反應生成物은1,1-diphenyl-2-amino-ethyl acetate 임을 알았다. 또한 이 開環反應은 aziridine環 안에 있는 窒素原子와 tertiary炭素原子사이의 結合이 切斷되어 中間體로서 carbonium이온이 形成되는 過程을 거쳐서 進行됨을 알았다.