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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 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

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ISBN:9781305957404
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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
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.) :
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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