Pd()-Catalyzed enantioselective C-H olefination toward the synthesis of -stereogenic phosphinamides
P -Stereogenic phosphorus compounds are important structural elements in chiral ligands or organocatalysts. Herein, we report a Pd( ii )-catalyzed enantioselective C-H olefination toward the synthesis of P -stereogenic phosphinamides using cheap commercially available l - p Glu-OH as a chiral ligand...
Saved in:
| Published in | Chemical communications (Cambridge, England) Vol. 6; no. 12; pp. 1623 - 1626 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Published |
06.02.2024
|
| Online Access | Get full text |
Cover
Loading…
| Abstract | P
-Stereogenic phosphorus compounds are important structural elements in chiral ligands or organocatalysts. Herein, we report a Pd(
ii
)-catalyzed enantioselective C-H olefination toward the synthesis of
P
-stereogenic phosphinamides using cheap commercially available
l
-
p
Glu-OH as a chiral ligand. A broad range of
P
-stereogenic phosphinamides were gained in good yields with high enantioselectivities (33 examples, up to 77% yield, 99% ee)
via
desymmetrization and kinetic resolution.
A Pd(
ii
)-catalyzed enantioselective C-H olefination toward the synthesis of
P
-stereogenic phosphines is reported. |
|---|---|
| AbstractList | P
-Stereogenic phosphorus compounds are important structural elements in chiral ligands or organocatalysts. Herein, we report a Pd(
ii
)-catalyzed enantioselective C-H olefination toward the synthesis of
P
-stereogenic phosphinamides using cheap commercially available
l
-
p
Glu-OH as a chiral ligand. A broad range of
P
-stereogenic phosphinamides were gained in good yields with high enantioselectivities (33 examples, up to 77% yield, 99% ee)
via
desymmetrization and kinetic resolution.
A Pd(
ii
)-catalyzed enantioselective C-H olefination toward the synthesis of
P
-stereogenic phosphines is reported. |
| Author | Chen, Zi-Jia Fan, Ling-Jie Zhou, Tao Shi, Bing-Feng Qian, Pu-Fan Xie, Pei-Pei Hu, Xinquan |
| AuthorAffiliation | Department of Chemistry Center of Chemistry for Frontier Technologies Ministry of Education Hangzhou Normal University College of Biological, Chemical Sciences and Engineering College of Material Chemistry and Chemical Engineering Zhejiang University of Technology Key Laboratory of Organosilicon Chemistry and Material Technology Jiaxing University College of Chemical Engineering Zhejiang University |
| AuthorAffiliation_xml | – name: Zhejiang University of Technology – name: Jiaxing University – name: Department of Chemistry – name: Center of Chemistry for Frontier Technologies – name: College of Chemical Engineering – name: Key Laboratory of Organosilicon Chemistry and Material Technology – name: Hangzhou Normal University – name: College of Material Chemistry and Chemical Engineering – name: Ministry of Education – name: Zhejiang University – name: College of Biological, Chemical Sciences and Engineering |
| Author_xml | – sequence: 1 givenname: Zi-Jia surname: Chen fullname: Chen, Zi-Jia – sequence: 2 givenname: Ling-Jie surname: Fan fullname: Fan, Ling-Jie – sequence: 3 givenname: Pei-Pei surname: Xie fullname: Xie, Pei-Pei – sequence: 4 givenname: Pu-Fan surname: Qian fullname: Qian, Pu-Fan – sequence: 5 givenname: Xinquan surname: Hu fullname: Hu, Xinquan – sequence: 6 givenname: Tao surname: Zhou fullname: Zhou, Tao – sequence: 7 givenname: Bing-Feng surname: Shi fullname: Shi, Bing-Feng |
| BookMark | eNqFjjFrwzAUhEVwIXGaJXvhje2gRK6s1JlNS8YOHbIFIT3XCrZk9ESC8-vjQqFjb_mOOw4uZ5kPHhlbF2JTCLnfWmmMUEK96hlbFHJXclVWx-zHqz1_k6Was5zoLCYVqlow82mfX3itk-7GG1pAr31ygbBDk9wFoeYHCB02zusp95DCVUcLqUWg0U8gRxAa4JQwYvhG7wwMbaChnSa9s0iP7KHRHeHql0v29PH-VR94JHMaout1HE9_z-V__R0-00ns |
| ContentType | Journal Article |
| DOI | 10.1039/d3cc05052a |
| DatabaseTitleList | |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1364-548X |
| EndPage | 1626 |
| ExternalDocumentID | d3cc05052a |
| GroupedDBID | --- -DZ -JG -~X 0-7 0R~ 29B 4.4 5GY 6J9 705 70J 70~ 7~J AAEMU AAGNR AAIWI AANOJ AAXHV AAXPP ABASK ABDVN ABGFH ABJNI ABRYZ ACBEA ACGFO ACGFS ACIWK ACLDK ACNCT ADMRA AENEX AETIL AFOGI AFVBQ AGKEF AGRSR AGSTE ALMA_UNASSIGNED_HOLDINGS ANUXI ASKNT AUDPV AZFZN BLAPV BSQNT C6K CS3 DU5 EBS ECGLT EE0 EF- F5P GNO HZ~ H~N IDZ IH2 J3I N9A O9- P2P R7B R7C R7D RAOCF RCNCU RPMJG RRA RRC RSCEA SJN SKA SKF SKH SLH TN5 TWZ UPT VH6 VQA WH7 X7L |
| ID | FETCH-rsc_primary_d3cc05052a3 |
| ISSN | 1359-7345 |
| IngestDate | Wed Feb 07 04:24:47 EST 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 12 |
| LinkModel | OpenURL |
| MergedId | FETCHMERGED-rsc_primary_d3cc05052a3 |
| Notes | Electronic supplementary information (ESI) available. CCDC For ESI and crystallographic data in CIF or other electronic format see DOI 2183918 https://doi.org/10.1039/d3cc05052a |
| PageCount | 4 |
| ParticipantIDs | rsc_primary_d3cc05052a |
| PublicationCentury | 2000 |
| PublicationDate | 20240206 |
| PublicationDateYYYYMMDD | 2024-02-06 |
| PublicationDate_xml | – month: 2 year: 2024 text: 20240206 day: 6 |
| PublicationDecade | 2020 |
| PublicationTitle | Chemical communications (Cambridge, England) |
| PublicationYear | 2024 |
| References_xml | – issn: 2011 publication-title: P-Stereogenic Ligands in Enantioselective Catalysis doi: Grabulosa |
| SSID | ssj0000158 |
| Score | 4.9654007 |
| Snippet | P
-Stereogenic phosphorus compounds are important structural elements in chiral ligands or organocatalysts. Herein, we report a Pd(
ii
)-catalyzed... |
| SourceID | rsc |
| SourceType | Publisher |
| StartPage | 1623 |
| Title | Pd()-Catalyzed enantioselective C-H olefination toward the synthesis of -stereogenic phosphinamides |
| Volume | 6 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1LT8JAEN4gHPRifBFfmD140JBF6JZtOZIGgkQNB0yIF0K7S2yiLeFxgKO_3Nnutl0NJuqBUrbQbpivM7PTmW8QuuY-s1zutkhQdzixed0hE27ZxLInHFSmM_Ebst758Yn1nu3-qDkqFD6MrKXV0q8Fm611Jf-RKoyBXGWV7B8km50UBmAf5AtbkDBsfyXjAVzQhbU88WQQZr0B51HIxJYwXiTtbWRWkEd61fhNTEMV9gNfU-bJJv7mYh3Bm2YkIZIxQcRwrTCozl7jxUx21n4PuU4yTNkMUoKBwKwsSUK3WflXol9VcxAj0ODpOpCXkPTDzBh0de0DWFAYzlA2Uo9NBiIk8Mqis6H69mBFuhrVOmABcpc5zszQsbTZIg5VLJI1oceYTWDxNDIVMzPxZxlatsFUjbK22PCRbbUGdSrJVDkNgqRfn2HzskzE_OAOKllOqwkL-FK7M7x_MEjIki6v2bRTklvaust_Da7JPG0Zk7gmwwO0r9cUuK0AcogKIjpCu17ayu8YBQN-c5uDBH8HCQaQYAMkWIEEAzpwBhIcT7EJEvwVJCeo0u0MvR6BCY5nisNknM-cllExiiNxijCnjLnUZixwwbEDZ87xqbxzG8IRFBzhM1Tefo7znw5coL0cApeouJyvRAW8uKV_pf_mT59GTlw |
| link.rule.ids | 315,786,790,27957,27958 |
| linkProvider | Royal Society of Chemistry |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Pd%28%29-Catalyzed+enantioselective+C-H+olefination+toward+the+synthesis+of+-stereogenic+phosphinamides&rft.jtitle=Chemical+communications+%28Cambridge%2C+England%29&rft.au=Chen%2C+Zi-Jia&rft.au=Fan%2C+Ling-Jie&rft.au=Xie%2C+Pei-Pei&rft.au=Qian%2C+Pu-Fan&rft.date=2024-02-06&rft.issn=1359-7345&rft.eissn=1364-548X&rft.volume=6&rft.issue=12&rft.spage=1623&rft.epage=1626&rft_id=info:doi/10.1039%2Fd3cc05052a&rft.externalDocID=d3cc05052a |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1359-7345&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1359-7345&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1359-7345&client=summon |