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In this study, chiral ligand 6 derived from inexpensive (R)-4hydroxyphenylglycine was used in the catalytic asymmetric Diels-Alder reaction between 7 and 8, thus resulting in the synthesis of the antipode of natural 1.
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In this study, chiral ligand 6 derived from inexpensive (R)-4hydroxyphenylglycine was used in the catalytic asymmetric Diels-Alder reaction between 7 and 8, thus resulting in the synthesis of the antipode of natural 1.
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During the scale-up studies, it was found that the enantioselectivity of this catalytic Diels-Alder reaction was improved to up to 96% ee (87% ee in Ref. [11]) by using strict temperature control and moisture exclusion.
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During the scale-up studies, it was found that the enantioselectivity of this catalytic Diels-Alder reaction was improved to up to 96% ee (87% ee in Ref. [11]) by using strict temperature control and moisture exclusion.
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See the Supporting Information for details
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a) See the Supporting Information for details;
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when, the catalytic asymmetric Diels-Alder reaction was conducted on greater than 10 g scales, a decline in the ee value was observed, probably because of the slight increase in the reaction temperature during the addition of substrates.
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b) when, the catalytic asymmetric Diels-Alder reaction was conducted on greater than 10 g scales, a decline in the ee value was observed, probably because of the slight increase in the reaction temperature during the addition of substrates.
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The hydrolysis of the enol TIPS ether provided a 1:1 mixture of C1 isomers. Although further conversion was described from one isomer (14) in the text, the other isomer was also utilized for the synthesis of intermediate 10 with comparable efficiency; see the Supporting Information for details.
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