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Anti-Selective Dihydroxylation Reactions of Monosubstituted and (E)-Ester Conjugated Allylic Amines by Bulky Alkyl Groups
The $O_sO_4$-catalyzed dihydroxylations of a monosubstituted allylic amine and $\gamma-amino-\alpha,\;\beta-unsaturated$ (E)-esters with bulky alkyl groups showed a high anti-selectivity. Since the acyclic conformation of N-acyloxy protected allylic amines was efficiently controlled by a bulky t-Bu...
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| Published in: | Bulletin of the Korean Chemical Society 2009, Vol.30 (5), p.1003-1008 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | Korean |
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| container_end_page | 1008 |
| container_issue | 5 |
| container_start_page | 1003 |
| container_title | Bulletin of the Korean Chemical Society |
| container_volume | 30 |
| creator | Jeon, Jong-Ho Kim, So-Hee Lee, Jong-Hyup Oh, Joon-Seok Park, Doh-Yeon Kim, Young-Gyu |
| description | The $O_sO_4$-catalyzed dihydroxylations of a monosubstituted allylic amine and $\gamma-amino-\alpha,\;\beta-unsaturated$ (E)-esters with bulky alkyl groups showed a high anti-selectivity. Since the acyclic conformation of N-acyloxy protected allylic amines was efficiently controlled by a bulky t-Bu or OBO ester group, the anti diastereoselectivity of >12.5:1 was obtained without applying a chiral reagent. The synthetic utility of the present method was demonstrated by a stereoselective and efficient synthesis of an $\alpha$-glucosidase inhibitor 15 from commercially available N-Cbz-L-serine 6 in 11 steps and 31% yield. |
| format | article |
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| identifier | ISSN: 0253-2964 |
| ispartof | Bulletin of the Korean Chemical Society, 2009, Vol.30 (5), p.1003-1008 |
| issn | 0253-2964 1229-5949 |
| language | kor |
| recordid | cdi_kisti_ndsl_JAKO200902727350921 |
| source | Free Full-Text Journals in Chemistry |
| title | Anti-Selective Dihydroxylation Reactions of Monosubstituted and (E)-Ester Conjugated Allylic Amines by Bulky Alkyl Groups |
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