2011
DOI: 10.1021/jo102140z
|View full text |Cite
|
Sign up to set email alerts
|

Highly cis-Selective Rh(I)-Catalyzed Cyclopropanation Reactions

Abstract: The performance of recently reported highly cis-diastereoselective Rh(I) cyclopropanation catalysts has been significantly improved by a systematic study of different reaction parameters (catalyst activation, solvent, temperature, stoichiometry). The catalyst efficiency and diastereoselectivity were enhanced by changing the activating agent from AgOTf to NaBArf. With this new system, the Rh(I) catalyst was shown to be a highly efficient and cis-diastereoselective cyclopropanation catalyst in reactions between … Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1

Citation Types

0
24
0

Year Published

2013
2013
2020
2020

Publication Types

Select...
5
4

Relationship

1
8

Authors

Journals

citations
Cited by 46 publications
(24 citation statements)
references
References 43 publications
0
24
0
Order By: Relevance
“…Note that the eco-tolerability of cyclopropanationr eactions can be further enhanced i) by using continuous flow methodologies due to the safe handling of hazardous reagents such as diazo compounds, [17][18][19][20] ii)bya pplying biomimeticc atalysts coupling very good catalytic activity with natural high chemical selectivity, [21][22][23][24][25][26] and iii)bye mploying unconventional catalytic systems such as supramolecular cage catalysts whichs imulate the working operandi of enzymes. [27][28][29][30] Amongst all the metal catalysts, metal porphyrins were very activea nd ruthenium, [31][32][33][34] osmium, [35,36] rhodium, [37][38][39] and iridium [40] porphyrin complexes have been extensively employed to promote cyclopropanationr eactions. In spite of the good catalytic efficiency of the above-mentioned porphyrin catalysts, their high cost and toxicity prompted the study of the more eco-friendly first-row transition metal porphyrins, such as cobalt [41][42][43][44][45][46] and iron [47][48][49][50][51][52][53][54] derivatives.…”
Section: Introductionmentioning
confidence: 99%
“…Note that the eco-tolerability of cyclopropanationr eactions can be further enhanced i) by using continuous flow methodologies due to the safe handling of hazardous reagents such as diazo compounds, [17][18][19][20] ii)bya pplying biomimeticc atalysts coupling very good catalytic activity with natural high chemical selectivity, [21][22][23][24][25][26] and iii)bye mploying unconventional catalytic systems such as supramolecular cage catalysts whichs imulate the working operandi of enzymes. [27][28][29][30] Amongst all the metal catalysts, metal porphyrins were very activea nd ruthenium, [31][32][33][34] osmium, [35,36] rhodium, [37][38][39] and iridium [40] porphyrin complexes have been extensively employed to promote cyclopropanationr eactions. In spite of the good catalytic efficiency of the above-mentioned porphyrin catalysts, their high cost and toxicity prompted the study of the more eco-friendly first-row transition metal porphyrins, such as cobalt [41][42][43][44][45][46] and iron [47][48][49][50][51][52][53][54] derivatives.…”
Section: Introductionmentioning
confidence: 99%
“…Pleasingly,t he para-methyl, para-tert-butyl, and para-methoxy derivatives were readily converted into the corresponding cyclopropanes 3b-d in excellent yields with complete diastereoselectivity in favor of the trans isomer, [20] and excellent enantiomeric excesses.Asimilar reactivity was observed for the metasubstituted aryl derivatives as 3e and 3f were obtained in excellent yields and 99 % ee. [22] Finally,weextended the scope to two other diazo ketones, 1b (R = CN) and 1c(R = CO 2 Me), which were readily converted into the expected cyclopropanes 3m and 3n in good yields, very high diastereoselectivity,and excellent ee values for 3n. [21] Thestereochemical outcome of the reaction is in agreement with the model depicted by Davies and co-workers.…”
Section: Zuschriftenmentioning
confidence: 99%
“…[19] Moreover,the presence of the benzofuran ring was well tolerated, and the corresponding cyclopropane 3l was isolated in high yield with high d.r.and ee values.Note that no side reaction on the benzofuran ring was observed. [22] Finally,weextended the scope to two other diazo ketones, 1b (R = CN) and 1c(R = CO 2 Me), which were readily converted into the expected cyclopropanes 3m and 3n in good yields, very high diastereoselectivity,and excellent ee values for 3n.…”
Section: Zuschriftenmentioning
confidence: 99%