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In addition to the formation of 4bb in 59% isolated yield, reduction of ynenoate 3bb produced complex, inseparable mixtures of byproducts consistent with 1,6-reduction that represent the remaining mass balance.
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In addition to the formation of 4bb in 59% isolated yield, reduction of ynenoate 3bb produced complex, inseparable mixtures of byproducts consistent with 1,6-reduction that represent the remaining mass balance.
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48
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18844403662
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Alkyne (S)- 4bb was readily reduced to ester (R)- SI-3, the antipode of which has previously been prepared in 87% ee
-
Alkyne (S)- 4bb was readily reduced to ester (R)- SI-3, the antipode of which has previously been prepared in 87% ee: Lopez, F.; Harutyunyan, S. R.; Meetsma, A.; Minnaard, A. J.; Feringa, B. L. Angew. Chem., Int. Ed. 2005, 44, 2752
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The absolute stereochemistry of the current CuH reduction is assigned by analogy. We also note that the synthesis of (R)- SI-3, constitutes the formal addition an alkyl group to an α,β-unsaturated ester. We believe that this 3-step sequence, comprised entirely of catalytic reactions, compares favorably to other known, asymmetric, alkyl conjugate addition reactions.
-
The absolute stereochemistry of the current CuH reduction is assigned by analogy. We also note that the synthesis of (R)- SI-3, constitutes the formal addition an alkyl group to an α,β-unsaturated ester. We believe that this 3-step sequence, comprised entirely of catalytic reactions, compares favorably to other known, asymmetric, alkyl conjugate addition reactions.
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50
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79957980121
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While the hydroalkynylations were routinely performed on a 1.0 mmol scale, the CuH reductions were typically performed on a 0.15-0.30 mmol scale. As a preliminary indication of scalability, the synthesis of alkyne 4ca was performed on a 0.75 mmol scale, and the reaction maintained excellent yield and enantioselectivity (98% yield, 99% ee).
-
While the hydroalkynylations were routinely performed on a 1.0 mmol scale, the CuH reductions were typically performed on a 0.15-0.30 mmol scale. As a preliminary indication of scalability, the synthesis of alkyne 4ca was performed on a 0.75 mmol scale, and the reaction maintained excellent yield and enantioselectivity (98% yield, 99% ee).
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Lactone 5 was synthesized using Otera's catalyst (1,3- diisothiocyanatotetrabutyldistannoxane)
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