Shrenik K. Shah -- PhD 1977

Scientific Career

Thesis Title Preparation, Reactions and Further Transformations of α-Lithio Selenenides and Selenoxides. Synthetic Transformations Based on Propargyl Selenides.
Research Summary Shrenik, after a year or so of making theoretically interesting organoselenium molecules, tackled the chemistry of metalated selenides and selenoxides, developing several interesting and useful transformations. He found that allyl propargyl selenide could be easily dimetalated to form the reagent we usually write as shown below, which was an effective double nucleophile. The propargyl selenide products, when oxidized under the right conditions, were transformed into enones.

One of the compounds Shrenik made using the monolithium reagent, the silyl ketone below, catalyzed a major effort on the chemistry of silyl ketones, developed by, among others, Rick Olson, Ron Holtan, Martha Kelly and Eric Eisenhart.

Shrenik also developed procedures for the in situ preparation of previously unknown α-lithio selenoxides, which were synthetically equivalent to vinyllithium reagents. These were also extensively studies by Flora Chow.

After finishing his thesis work at Wisconsin, Shrenik did a post-doc in Bob Coates laboratory at the U. of Illinois.
  1. "Organoselenium Chemistry. α-Lithio Selenoxides and Selenides: Preparation and Further Transformation to Olefins, Dienes and Allylic Alcohols," H. J. Reich and S. K. Shah, J. Am. Chem. Soc. 1975, 97, 3250.

  2. "Selenium Stabilized Anions. Synthetic Transformations Based on Propargyl Selenoxides," H. J. Reich and S. K. Shah, J. Am. Chem. Soc. 1977, 99, 263.

  3. "Selenium Stabilized Anions. Selenoxide syn-Elimination and Sila-Pummerer Rearrangement of α-Silyl Selenoxides," H. J. Reich and S. K. Shah, J. Org. Chem. 1977, 42, 1773.

  4. "Selenium Stabilized Carbanions. Preparation of α-Lithio Selenides and Application to the Synthesis of Olefins by Reductive Elimination of β-Hydroxy Selenides and Selenoxide Syn Elimination," H. J. Reich, F. Chow and S. K. Shah, J. Am. Chem. Soc. 1979, 101, 6638. PDF

  5. "Selenium Stabilized Carbanions. α-Lithio Selenoxides as Reagents for the Synthesis of Olefins, Allyl Alcohols and Dienes," H. J. Reich, S. K. Shah and F. Chow, J. Am. Chem. Soc. 1979, 101, 6648. PDF

  6. "Selenium Stabilized Anions. Preparation of α,β-Unsaturated Carbonyl Compounds Using Propargyl Selenides. Synthesis of (+)-7-Hydroxymyoporone," H. J. Reich, S. K. Shah, P. M. Gold and R. E. Olson, J. Am. Chem. Soc. 1981, 103, 3112. PDF

Current Position Senior Research Fellow - medicinal chemistry, drug discovery
Merck Sharp and Dohme Research

For comments, additions and corrections, send e-mail to Hans J. Reich