Directed RhI-Catalyzed Asymmetric Hydroboration of Prochiral 1-Arylcycloprop-2-Ene-1-Carboxylic Acid Derivatives

A full account on rhodium-catalyzed asymmetric, directed hydroboration of functionalized prochiral cyclopropenes affording enantiomerically enriched cyclopropylboronates is reported. The scope and limitations of two alternate directing groups, ester and carboxamide, are evaluated. It was found that hydroboration of esters appeared to be more sensitive to substitution in the aromatic ring of the substrates. Specifically, ortho-halogens were detrimental for diastereo- and enantioselectivity, possibly because of additional coordination with rhodium. In contrast, more Lewis-basic amide directing groups allowed for stronger chelation to the transition metal, leading to consistently high diastereo- and enantioselectivity in hydroboration across a broader range of substrates. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Авторы
Edwards A.1 , Rubina M. 1, 2 , Rubin M.1, 3
Редакторы
-
Издательство
Wiley-VCH Verlag
Номер выпуска
6
Язык
Английский
Страницы
1394-1403
Статус
Опубликовано
Подразделение
-
Номер
-
Том
24
Год
2018
Организации
  • 1 Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, United States
  • 2 Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 3 Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol, 355009, Russian Federation
Ключевые слова
asymmetric catalysis; cyclopropenes; hydroboration; protecting groups; rhodium
Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/6897/