DBU-mediated diastereoselective aldol-type cyanomethylation of isatins
| Title | DBU-mediated diastereoselective aldol-type cyanomethylation of isatins |
| Publication Type | Journal Article |
| Year of Publication | 2017 |
| Authors | Rao, VUBhaskar, Kumar, K, Das, T, Vanka, K |
| Journal | Journal of Organic Chemistry |
| Volume | 82 |
| Issue | 8 |
| Pagination | 4489-4496 |
| Date Published | APR |
| Type of Article | Article |
| Abstract | An efficient, metal-free approach to 3-substituted 3-hydroxybxindole by DBU-mediated highly diastereoselective addition of aryl acetonitrile to N-protected isatin under mild conditions has been developed. The reaction proceeds smoothly to produce respective cyanomethylated adducts in good yield and excellent diastereoselectivity. Further transformation of the cyanide group allowed the synthesis of an advance intermediate of corresponding (+/-) CPC analogue. The mechanistic insight :toward the aldol-type cyanomethylation, of N-tritylisatin with benzyl cyanide was obtained by DFT calculations. |
| DOI | 10.1021/acs.joc.7b00512 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 4.785 |
Divison category:
Physical and Materials Chemistry
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