Seminar


Department of Chemistry
Indian Institute of Technology Delhi

Stereodefined Carbometallation of Carbocycles: New Tricks with Old Odds

Dr. Sudipta Raha Roy
Institut Català d’Investigació Química (ICIQ), Tarragona, Spain. Email: sudiptaraharoy@gmail.com

Date: February 16th 2018 (Friday)
Time: 4:00 PM
Venue: Committee Room, Chemistry Department, 6th Floor

In recent years, there have been emerging trends in integrating multiple catalytic cycles in one pot1 which offers a vast array of strategies for the synthesis of fine chemicals.2 However, construction of carbon-carbon (C-C) bonds, particularly with concomitant control of newly formed asymmetric centers, is of paramount importance for the development of synthetic routes to complex organic molecules.3 Thus, C-C bond formation reactions through the use of organometallic species are expected to be a major driver for the synthesis of economically important fine chemicals.4 In the repertoire of C-C bond formation with organometallic species, organocopper derivatives occupy a significant place due to their high stereo- and chemo-selectivity5, which enables them to add smoothly to the multiple bonds even in the presence of other functionalities. Moreover addition of Et2Zn and CH2I2 (Zinc Homologation), to the carbocuprate derivative will also allow to incorporate one additional functionalized carbo-metallic bond which intern may facilitate the formation of acyclic adducts possessing a challenging all-carbon quaternary stereocenters. As a part of our ongoing interest on the strained molecular system, the new stereodefined tandem reactions6 of functionalized cyclopropenes and cyclobutenes to generate all-carbon quaternary stereocenters will be discussed in this lecture.

    References:
  1. A. S. Goldman, A. H. Roy, Z. Huang, R. Ahuja, W. Schinski, M. Brookhart, Science 2006, 312, 257.
  2. R. W. Dugger, J. A. Ragan and D. H. B. Ripin, Org. Process Res. Dev., 2005, 9, 253.
  3. Y. Minko, M. Pasco, L. Lercher, M. Botoshansky, I. Marek, Nature, 2012, 490, 522.
  4. a) L. Ackermann, R. Vicente, A.R. Kapdi, Angew. Chem. Int. Ed., 2009, 48, 9792; b) S. H. Cho, J. Y. Kim, S. Y. Lee, S. Chang, Angew. Chem. Int. Ed., 2009, 48, 9127.
  5. a) G. Sklute , D. Amsallem , A. Shabli , J. P. Varghese, I. Marek, J. Am. Chem. Soc., 2003, 125, 11776; b) P.O. Delaye, D. Didier, I. Marek, Angew. Chem. Int. Ed., 2013, 52, 5333.
  6. a) S. Raha Roy, D. Didier, A. Kleiner, I. Marek, Chem. Sci., 2016, 7, 5989; b) S. Raha Roy, H. Eijsberg, J. Bruffaerts, I. Marek, Chem. Sci., 2017, 8, 334.


All are cordially invited to attend.
Convener (Seminars)