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

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
› Author Affiliations
Further Information

Publication History

Received: 10 February 2014

Accepted after revision: 19 March 2014

Publication Date:
10 April 2014 (online)

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

 
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