Synlett 2014; 25(09): 1246-1252
DOI: 10.1055/s-0033-1341201
letter
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Interceptive Decarboxylative Addition of Allyl Car­bonates with Carbonyl Group

Autoren

  • T. V. Baiju

    a   Academy of Scientific and Innovative Research (AcSIR), New Delhi 110001, India
    b   Organic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695019, India   Fax: +91(471)2491712   eMail: radhu2005@gmail.com
  • Nayana Joseph

    b   Organic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695019, India   Fax: +91(471)2491712   eMail: radhu2005@gmail.com
  • Jainu Ajit

    b   Organic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695019, India   Fax: +91(471)2491712   eMail: radhu2005@gmail.com
  • Praveen Prakash

    b   Organic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695019, India   Fax: +91(471)2491712   eMail: radhu2005@gmail.com
  • K. V. Radhakrishnan*

    a   Academy of Scientific and Innovative Research (AcSIR), New Delhi 110001, India
    b   Organic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695019, India   Fax: +91(471)2491712   eMail: radhu2005@gmail.com
  • Sunil Varughese

    c   Inorganic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695019, India
  • Yoshinori Yamamoto*

    d   WPI-AIMR (Advanced Institute for Materials Research), Tohoku University, Katahira 2-1-1, Aobaku, Sendai 980-8577, Japan   eMail: yoshi@mail.tains.tohoku.ac.jp
Weitere Informationen

Publikationsverlauf

Received: 10. Februar 2014

Accepted after revision: 19. März 2014

Publikationsdatum:
10. April 2014 (online)


Graphical Abstract

Abstract

The first palladium-catalyzed interceptive decarboxylative 1,4-addition of allyl carbonates with squarates is reported. Interestingly, the C-3 carbonyl group of N-substituted isatins undergoes smooth decarboxylative 1,2-addition with allyl carbonates. This transformation offers a straightforward method for the synthesis of spiro-oxepane-fused 2-oxindole.

Supporting Information