Scalable synthesis of a new enantiomerically pure π-extended rigid amino indanol
A convenient route to a benzo-fused amino indanol chiral controller is disclosed. The synthesis is based on a newly optimized entry to 3 H-benz(e)indene that can be performed on decagram scale with no purification of intermediates. Subsequent oxidation, classical resolution, and Ritter steps give th...
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| Veröffentlicht in: | Tetrahedron letters 2012-01, Vol.53 (1), p.15-18 |
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| creator | Rendina, Victor L. Goetz, Samantha A. Neitzel, Angelika E. Kaplan, Hilan Z. Kingsbury, Jason S. |
| description | A convenient route to a benzo-fused amino indanol chiral controller is disclosed. The synthesis is based on a newly optimized entry to 3
H-benz(e)indene that can be performed on decagram scale with no purification of intermediates. Subsequent oxidation, classical resolution, and Ritter steps give the target synthon in >98% ee. The resolution features (
S)-naproxen as an inexpensive and highly crystalline resolving agent. Conversion of the amino alcohol to its bis(oxazolinyl)-propane is also reported. A solid state structure of the CuCl
2–box complex shows preservation of the distorted square planar geometry found in the parent CuCl
2(indanyl-box) despite greater steric crowding by the blocking groups. |
| doi_str_mv | 10.1016/j.tetlet.2011.10.144 |
| format | Article |
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H-benz(e)indene that can be performed on decagram scale with no purification of intermediates. Subsequent oxidation, classical resolution, and Ritter steps give the target synthon in >98% ee. The resolution features (
S)-naproxen as an inexpensive and highly crystalline resolving agent. Conversion of the amino alcohol to its bis(oxazolinyl)-propane is also reported. A solid state structure of the CuCl
2–box complex shows preservation of the distorted square planar geometry found in the parent CuCl
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H-benz(e)indene that can be performed on decagram scale with no purification of intermediates. Subsequent oxidation, classical resolution, and Ritter steps give the target synthon in >98% ee. The resolution features (
S)-naproxen as an inexpensive and highly crystalline resolving agent. Conversion of the amino alcohol to its bis(oxazolinyl)-propane is also reported. A solid state structure of the CuCl
2–box complex shows preservation of the distorted square planar geometry found in the parent CuCl
2(indanyl-box) despite greater steric crowding by the blocking groups.</description><subject>3 H-Benz(e)indene</subject><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Amino indanol</subject><subject>Asymmetric catalysis</subject><subject>Bis(oxazoline)</subject><subject>Blocking</subject><subject>Chemistry</subject><subject>Conversion</subject><subject>Crystal structure</subject><subject>Distortion</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Organic chemistry</subject><subject>Parents</subject><subject>Preparations and properties</subject><subject>Purification</subject><subject>Ritter reaction</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp9UE1LxDAUDKLguvoPPOQieGlNmvTrIoj4BQsi6jmkyYtmadM1yap78x_6l2zt4tF3eTDMvDczCB1TklJCi7NlGiG2ENOMUJqOKOc7aEarkiUsr-gumhHCScIJq_fRQQhLMkxRkRl6eFSylU0LOGxcfIVgA-4NltjBBwYnXbR9B94OrHaDV2sP-Psrgc8IToPG3r5YjWVnXY-t09L17SHaM7INcLTdc_R8ffV0eZss7m_uLi8WiWJFHRNDC9AlZaBJ0dCKQ9bIojEgM8UNkRWrm0zlmlPNjCZVThsCDauY5JXkjcnYHJ1Od1e-f1tDiKKzQUHbSgf9Oghacl6UBcvqgconqvJ9CB6MWHnbSb8RlIixQbEUU4NibPAX5XyQnWw_yDDkN146ZcOfNstZPhganZxPPBjivlvwIigLToG2HlQUurf_P_oBWcqKaA</recordid><startdate>20120104</startdate><enddate>20120104</enddate><creator>Rendina, Victor L.</creator><creator>Goetz, Samantha A.</creator><creator>Neitzel, Angelika E.</creator><creator>Kaplan, Hilan Z.</creator><creator>Kingsbury, Jason S.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20120104</creationdate><title>Scalable synthesis of a new enantiomerically pure π-extended rigid amino indanol</title><author>Rendina, Victor L. ; Goetz, Samantha A. ; Neitzel, Angelika E. ; Kaplan, Hilan Z. ; Kingsbury, Jason S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c369t-f16ed713ed06b184e2ba6bfea2c4f0a839b2c5d41d3fd0851b0eb383a48a4bf23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>3 H-Benz(e)indene</topic><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Amino indanol</topic><topic>Asymmetric catalysis</topic><topic>Bis(oxazoline)</topic><topic>Blocking</topic><topic>Chemistry</topic><topic>Conversion</topic><topic>Crystal structure</topic><topic>Distortion</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Organic chemistry</topic><topic>Parents</topic><topic>Preparations and properties</topic><topic>Purification</topic><topic>Ritter reaction</topic><topic>Synthesis (chemistry)</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rendina, Victor L.</creatorcontrib><creatorcontrib>Goetz, Samantha A.</creatorcontrib><creatorcontrib>Neitzel, Angelika E.</creatorcontrib><creatorcontrib>Kaplan, Hilan Z.</creatorcontrib><creatorcontrib>Kingsbury, Jason S.</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rendina, Victor L.</au><au>Goetz, Samantha A.</au><au>Neitzel, Angelika E.</au><au>Kaplan, Hilan Z.</au><au>Kingsbury, Jason S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Scalable synthesis of a new enantiomerically pure π-extended rigid amino indanol</atitle><jtitle>Tetrahedron letters</jtitle><date>2012-01-04</date><risdate>2012</risdate><volume>53</volume><issue>1</issue><spage>15</spage><epage>18</epage><pages>15-18</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><coden>TELEAY</coden><abstract>A convenient route to a benzo-fused amino indanol chiral controller is disclosed. The synthesis is based on a newly optimized entry to 3
H-benz(e)indene that can be performed on decagram scale with no purification of intermediates. Subsequent oxidation, classical resolution, and Ritter steps give the target synthon in >98% ee. The resolution features (
S)-naproxen as an inexpensive and highly crystalline resolving agent. Conversion of the amino alcohol to its bis(oxazolinyl)-propane is also reported. A solid state structure of the CuCl
2–box complex shows preservation of the distorted square planar geometry found in the parent CuCl
2(indanyl-box) despite greater steric crowding by the blocking groups.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2011.10.144</doi><tpages>4</tpages></addata></record> |
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| language | eng |
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| source | Access via ScienceDirect (Elsevier) |
| subjects | 3 H-Benz(e)indene Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Amino indanol Asymmetric catalysis Bis(oxazoline) Blocking Chemistry Conversion Crystal structure Distortion Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Organic chemistry Parents Preparations and properties Purification Ritter reaction Synthesis (chemistry) Tetrahedrons |
| title | Scalable synthesis of a new enantiomerically pure π-extended rigid amino indanol |
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