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The organocatalyzed domino Michael–aldol reaction revisited. Synthesis of enantioenriched 3-hydroxycyclohexanone derivatives by reaction of enals with α,α′-diaryl-substituted acetone
The reaction of enals with α,α′-diaryl-substituted acetones (p K a > 18) catalyzed by ( S )-1-(2-pyrrolidinylmethyl) pyrrolidine provides direct access to enantioenriched 2,5,6-trisubstituted-3-hydroxy cyclohexanones. The process constitutes a highly stereoselective organocatalytic tandem Michael...
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| Published in: | RSC advances 2015-01, Vol.5 (81), p.65975-65981 |
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| Main Authors: | , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c300t-e75ed49d9c7b6a666a1e3cc7aad0dbbd4f6ec7af254ae83be2f5fed9585a5f9d3 |
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| cites | cdi_FETCH-LOGICAL-c300t-e75ed49d9c7b6a666a1e3cc7aad0dbbd4f6ec7af254ae83be2f5fed9585a5f9d3 |
| container_end_page | 65981 |
| container_issue | 81 |
| container_start_page | 65975 |
| container_title | RSC advances |
| container_volume | 5 |
| creator | Guevara-Pulido, James O. Andrés, José M. Pedrosa, Rafael |
| description | The reaction of enals with α,α′-diaryl-substituted acetones (p
K
a
> 18) catalyzed by (
S
)-1-(2-pyrrolidinylmethyl) pyrrolidine provides direct access to enantioenriched 2,5,6-trisubstituted-3-hydroxy cyclohexanones. The process constitutes a highly stereoselective organocatalytic tandem Michael-intramolecular aldol reaction. It has been demonstrated that the stereoselection is dependent on the reaction conditions because only
syn
diastereoisomers are able to cyclize, and that
anti
diastereoisomers participate in a retro-Michael process decreasing the enantioselection. |
| doi_str_mv | 10.1039/C5RA11215J |
| format | article |
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S
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syn
diastereoisomers are able to cyclize, and that
anti
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K
a
> 18) catalyzed by (
S
)-1-(2-pyrrolidinylmethyl) pyrrolidine provides direct access to enantioenriched 2,5,6-trisubstituted-3-hydroxy cyclohexanones. The process constitutes a highly stereoselective organocatalytic tandem Michael-intramolecular aldol reaction. It has been demonstrated that the stereoselection is dependent on the reaction conditions because only
syn
diastereoisomers are able to cyclize, and that
anti
diastereoisomers participate in a retro-Michael process decreasing the enantioselection.</description><subject>Acetone</subject><subject>Aldehydes</subject><subject>Cascade chemical reactions</subject><subject>Chemical reactions</subject><subject>Cyclohexanone</subject><subject>Derivatives</subject><subject>Synthesis (chemistry)</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNpNkU1O5DAQhSMEEojpDSfwEiHC2Ens7ixRC2YGgZD4WUcVu0KM3DZju5vOrLgDJ4E1Z-AQfRKMeiSoTVVJr76n0suyPUaPGC3rn1N-dcxYwfjZRrZT0ErkBRX15rd5OxuFcE9TCc4KwXayt5seifN3YJ2ECGb4h4ooN9PWkQste0CzenoGo5whHkFG7WwaFjroiOqIXA829hh0IK4jaMEmAVqfLhOnzPtBebcc5CCN63GZXCwShV4vIOoFBtIOX9g1wQTyqGNP3l8O319WT6-50uAHk4d5G6KO82RLQGJMpB_ZVpf0OPrfd7Pb05Ob6e_8_PLXn-nxeS5LSmOOY46qqlUtx60AIQQwLKUcAyiq2lZVncC0dQWvACdli0XHO1Q1n3DgXa3K3Wx_zX3w7u8cQ2xmOkg0Biy6eWjYhPNSVFVNk_RgLZXeheCxax68nqUHGkabz5Sar5TKDzW8j3c</recordid><startdate>20150101</startdate><enddate>20150101</enddate><creator>Guevara-Pulido, James O.</creator><creator>Andrés, José M.</creator><creator>Pedrosa, Rafael</creator><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20150101</creationdate><title>The organocatalyzed domino Michael–aldol reaction revisited. Synthesis of enantioenriched 3-hydroxycyclohexanone derivatives by reaction of enals with α,α′-diaryl-substituted acetone</title><author>Guevara-Pulido, James O. ; Andrés, José M. ; Pedrosa, Rafael</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c300t-e75ed49d9c7b6a666a1e3cc7aad0dbbd4f6ec7af254ae83be2f5fed9585a5f9d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Acetone</topic><topic>Aldehydes</topic><topic>Cascade chemical reactions</topic><topic>Chemical reactions</topic><topic>Cyclohexanone</topic><topic>Derivatives</topic><topic>Synthesis (chemistry)</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Guevara-Pulido, James O.</creatorcontrib><creatorcontrib>Andrés, José M.</creatorcontrib><creatorcontrib>Pedrosa, Rafael</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Guevara-Pulido, James O.</au><au>Andrés, José M.</au><au>Pedrosa, Rafael</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The organocatalyzed domino Michael–aldol reaction revisited. Synthesis of enantioenriched 3-hydroxycyclohexanone derivatives by reaction of enals with α,α′-diaryl-substituted acetone</atitle><jtitle>RSC advances</jtitle><date>2015-01-01</date><risdate>2015</risdate><volume>5</volume><issue>81</issue><spage>65975</spage><epage>65981</epage><pages>65975-65981</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>The reaction of enals with α,α′-diaryl-substituted acetones (p
K
a
> 18) catalyzed by (
S
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syn
diastereoisomers are able to cyclize, and that
anti
diastereoisomers participate in a retro-Michael process decreasing the enantioselection.</abstract><doi>10.1039/C5RA11215J</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2046-2069 |
| ispartof | RSC advances, 2015-01, Vol.5 (81), p.65975-65981 |
| issn | 2046-2069 2046-2069 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1855364490 |
| source | Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list) |
| subjects | Acetone Aldehydes Cascade chemical reactions Chemical reactions Cyclohexanone Derivatives Synthesis (chemistry) |
| title | The organocatalyzed domino Michael–aldol reaction revisited. Synthesis of enantioenriched 3-hydroxycyclohexanone derivatives by reaction of enals with α,α′-diaryl-substituted acetone |
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