| Chapter title |
Organocatalytic Site-Selective Acylation of Carbohydrates and Polyol Compounds
|
|---|---|
| Chapter number | 662 |
| Book title |
Site-Selective Catalysis
|
| Published in |
Topics in current chemistry, October 2015
|
| DOI | 10.1007/128_2015_662 |
| Pubmed ID | |
| Book ISBNs |
978-3-31-926331-1, 978-3-31-926333-5
|
| Authors |
Yoshihiro Ueda, Takeo Kawabata |
| Editors |
Takeo Kawabata |
| Abstract |
Development and scope of conventionally difficult molecular transformation on site-selective acylation of carbohydrates and polyol compounds are described. A salient feature is that the site-selectivity can be controlled independently from the intrinsic reactivity of the substrate, i.e., catalyst-controlled selectivity. Therefore, some substrates undergo acylation with reversal of their intrinsic reactivity. The mechanistic aspects of catalyst-controlled site-selective acylation are discussed with the emphasis on the strategy relying on the accelerative reaction rather than the decelerative one. An unconventional retrosynthetic route based on catalyst-controlled site-selective acylation is proposed toward extremely short-step total synthesis of natural glycosides of an ellagitannin family. Application to the late-stage functionalization of the complex natural products of biological interest is also described. |
Mendeley readers
Geographical breakdown
| Country | Count | As % |
|---|---|---|
| Unknown | 9 | 100% |
Demographic breakdown
| Readers by professional status | Count | As % |
|---|---|---|
| Student > Ph. D. Student | 2 | 22% |
| Professor | 1 | 11% |
| Student > Bachelor | 1 | 11% |
| Student > Master | 1 | 11% |
| Unknown | 4 | 44% |
| Readers by discipline | Count | As % |
|---|---|---|
| Chemistry | 5 | 56% |
| Unknown | 4 | 44% |