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Asymmetric Michael Addition of Dimethyl Malonate to 2 Cyclopenten-1-one Catalyzed by a Heterobimetallic Complex

Fastuca, Nicholas J. and Wong, Alice R. and Mak, Victor W. and Reisman, Sarah E. (2020) Asymmetric Michael Addition of Dimethyl Malonate to 2 Cyclopenten-1-one Catalyzed by a Heterobimetallic Complex. Organic Syntheses, 97 . pp. 327-338. ISSN 2333-3553. https://resolver.caltech.edu/CaltechAUTHORS:20210125-140300975

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Abstract

A. Preparation of GaNa-(S)-BINOL((S)-2) Solution (0.05 M).2 A flame-dried 1L, three-necked round-bottomed flask with 24/40 joints and a 1.5" Teflon coated egg-shaped magnetic stir bar is brought into a nitrogen filled glovebox (Note 2). The flask is charged with gallium (III) chloride (5.0 g, 28.4 mmol, 1.0 equiv) (Notes 3 and 4). The flask is sealed with three rubber septa (one of which is fitted with an internal temperature probe) brought out of the glovebox, and put under positive pressure of nitrogen via a needle attached to a nitrogen line. Another flame-dried 1L, three-necked round-bottomed flask with 24/40 joints and a 1.5" Teflon coated egg-shaped magnetic stir bar is charged with (S)-(-)-1,1'-bi(2-naphthol) ((S)-BINOL, (S)-1) (16.26 g, 56.8 mmol, 2.0 equiv) (Note 5). The flask is sealed with three rubber septa (one of which is fitted with a thermometer) and evacuated and backfilled with nitrogen three times (5 minutes under vacuum per cycle). A flame-dried 500 mL round-bottomed flask with a 24/40 joint and a 1" Teflon coated egg-shaped magnetic stir bar is charged with sodium tert -butoxide (10.92 g, 113.6 mmol, 4.0 equiv) (Note 6). The flask is sealed with a rubber septum and evacuated and backfilled with nitrogen three times (5 minutes under vacuum per cycle).


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.15227/orgsyn.097.0327DOIArticle
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2020 Organic Syntheses, Inc. Published on the Web 11/6/2020.
Record Number:CaltechAUTHORS:20210125-140300975
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20210125-140300975
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:107715
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:26 Jan 2021 19:25
Last Modified:26 Jan 2021 19:25

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