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...

Description complète

Enregistré dans:

Détails bibliographiques
Auteurs principaux:	Rubin, M. A., Рубин, М. А.
Format:	Статья
Langue:	English
Publié:	Wiley-VCH Verlag 2018
Sujets:	Asymmetric catalysis Cyclopropenes Hydroboration Protecting groupsr Rhodium
Accès en ligne:	https://www.scopus.com/record/display.uri?eid=2-s2.0-85038430036&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=nort+caucas+fed+univ&sid=2cf89b62d1430faea2513c9ed4dc1d39&sot=afnl&sdt=afsp&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&relpos=14&citeCnt=1&searchTerm= https://dspace.ncfu.ru:443/handle/20.500.12258/217
Tags:	Ajouter un tag Pas de tags, Soyez le premier à ajouter un tag!

id	ir-20.500.12258-217
record_format	dspace
spelling	ir-20.500.12258-2172020-07-09T12:33:55Z Directed RhI-catalyzed asymmetric hydroboration of prochiral 1-arylcycloprop-2-ene-1-carboxylic acid derivatives Rubin, M. A. Рубин, М. А. Asymmetric catalysis Cyclopropenes Hydroboration Protecting groupsr Rhodium 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 2018-05-18T13:45:38Z 2018-05-18T13:45:38Z 2018 Статья Edwards, A., Rubina, M., Rubin, M. Directed RhI-catalyzed asymmetric hydroboration of prochiral 1-arylcycloprop-2-ene-1-carboxylic acid derivatives // Chemistry - A European Journal. - 2018. - Volume 24. - Issue 6. - pp. 1394-1403. https://www.scopus.com/record/display.uri?eid=2-s2.0-85038430036&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=nort+caucas+fed+univ&sid=2cf89b62d1430faea2513c9ed4dc1d39&sot=afnl&sdt=afsp&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&relpos=14&citeCnt=1&searchTerm= https://dspace.ncfu.ru:443/handle/20.500.12258/217 en Chemistry - A European Journal application/pdf application/pdf Wiley-VCH Verlag
institution	СКФУ
collection	Репозиторий
language	English
topic	Asymmetric catalysis Cyclopropenes Hydroboration Protecting groupsr Rhodium
spellingShingle	Asymmetric catalysis Cyclopropenes Hydroboration Protecting groupsr Rhodium Rubin, M. A. Рубин, М. А. Directed RhI-catalyzed asymmetric hydroboration of prochiral 1-arylcycloprop-2-ene-1-carboxylic acid derivatives
description	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
format	Статья
author	Rubin, M. A. Рубин, М. А.
author_facet	Rubin, M. A. Рубин, М. А.
author_sort	Rubin, M. A.
title	Directed RhI-catalyzed asymmetric hydroboration of prochiral 1-arylcycloprop-2-ene-1-carboxylic acid derivatives
title_short	Directed RhI-catalyzed asymmetric hydroboration of prochiral 1-arylcycloprop-2-ene-1-carboxylic acid derivatives
title_full	Directed RhI-catalyzed asymmetric hydroboration of prochiral 1-arylcycloprop-2-ene-1-carboxylic acid derivatives
title_fullStr	Directed RhI-catalyzed asymmetric hydroboration of prochiral 1-arylcycloprop-2-ene-1-carboxylic acid derivatives
title_full_unstemmed	Directed RhI-catalyzed asymmetric hydroboration of prochiral 1-arylcycloprop-2-ene-1-carboxylic acid derivatives
title_sort	directed rhi-catalyzed asymmetric hydroboration of prochiral 1-arylcycloprop-2-ene-1-carboxylic acid derivatives
publisher	Wiley-VCH Verlag
publishDate	2018
url	https://www.scopus.com/record/display.uri?eid=2-s2.0-85038430036&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=nort+caucas+fed+univ&sid=2cf89b62d1430faea2513c9ed4dc1d39&sot=afnl&sdt=afsp&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&relpos=14&citeCnt=1&searchTerm= https://dspace.ncfu.ru:443/handle/20.500.12258/217
work_keys_str_mv	AT rubinma directedrhicatalyzedasymmetrichydroborationofprochiral1arylcycloprop2ene1carboxylicacidderivatives AT rubinma directedrhicatalyzedasymmetrichydroborationofprochiral1arylcycloprop2ene1carboxylicacidderivatives
_version_	1760600632018862080

Directed RhI-catalyzed asymmetric hydroboration of prochiral 1-arylcycloprop-2-ene-1-carboxylic acid derivatives

Documents similaires