Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Introduction to chemistry
Chemistry is a branch of science that deals with the analysis of material and the substances that comprise it. It also manages the properties of these substances and their reactions to form new substances. It is basically centered on particles and atoms …
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Chemistry problem
In F. Dean Toste's 2007 total synthesis of (+)-Fawcettimine (Angew Chem, 46 (40), 7671-7673), a Robinson Annulation was a critical first step in the reaction of ketoester (1) with crotonaldehyde (2) to provide 3 on a multi-gram scale in high yield with an important stereocenter set (R) in high ee (88%) by the use of a proline-derived chiral catalyst. Not worrying about the stereocenters, a detailed, step-wise, arrow pushing mechanisms for the Robinson Annulation to provide 3 is shown. Select the best answer that fills in both missing components correctly in the boxes shown for 1.) and 2.). The R group is an allyl group in all answers. 10% Proline-derived chiral catalyst O'Bu NaOH (aq), 0°C, 60h O'Bu 1 2 3 Mechanism 1.) O'Bu O'Bu O'Bu O'Bu e:ö: :0: R. : OH 1 H. R= Ally OH 2) R. O'Bu R. O'Bu O'Bu :0: но
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Transcribed Image Text:In F. Dean Toste's 2007 total synthesis of (+)-Fawcettimine (Angew Chem, 46 (40), 7671-7673), a Robinson Annulation was a critical first step in the reaction of ketoester (1) with crotonaldehyde (2) to provide 3 on a multi-gram scale in high yield with an important stereocenter set (R) in high ee (88%) by the use of a proline-derived chiral catalyst. Not worrying about the stereocenters, a detailed, step-wise, arrow pushing mechanisms for the Robinson Annulation to provide 3 is shown. Select the best answer that fills in both missing components correctly in the boxes shown for 1.) and 2.). The R group is an allyl group in all answers. 10% Proline-derived chiral catalyst O'Bu NaOH (aq), 0°C, 60h O'Bu 1 2 3 Mechanism 1.) O'Bu O'Bu O'Bu O'Bu e:ö: :0: R. : OH 1 H. R= Ally OH 2) R. O'Bu R. O'Bu O'Bu :0: но
c.) 1.) b.) 1) 1 a) 1.) 2) 2) 2) :0: :0: :: R. O'Bu R O'Bu O'Bul ****! HO HO но f.) 1.) 1 e) 1.) 1. d) 1.) 2) 2) :0: 2) :0: :0: R R. O'Bu O'Bu R. O'Bu ** HO HO a.) O b.) :
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Transcribed Image Text:c.) 1.) b.) 1) 1 a) 1.) 2) 2) 2) :0: :0: :: R. O'Bu R O'Bu O'Bul ****! HO HO но f.) 1.) 1 e) 1.) 1. d) 1.) 2) 2) :0: 2) :0: :0: R R. O'Bu O'Bu R. O'Bu ** HO HO a.) O b.) :
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