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Volumn 36, Issue 1, 2007, Pages 44-45

Catalytic asymmetric addition of alkynylzinc reagents to nitrones

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EID: 34247205362 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2007.44 Document Type: Article

Times cited : (19)

References (21)

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16
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- The numbers in front of the reagents in Schemes 1 and 2 indicate molar amounts of the reagents used.
- The numbers in front of the reagents in Schemes 1 and 2 indicate molar amounts of the reagents used.

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18
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- The optically pure (S)-N-propargylic hydroxylamine 4ba, was obtained as follows: The enantiomerically rich (S)-4ba (93% ee, obtained by asymmetric addition using a stoichiometric amount of (S,S)-DTBT,3 was treated with (S)-camphanic chloride and Et3N in the presence of a catalytic amount of 4-(N,N-dimethylamino)pyridine in CH2Cl2 to give the corresponding ester (74, Recrystallization from toluene/hexane gave the diastereomerically pure ester. The absolute configuration of the ester was determined to be S,S by X-ray crystallographic analysis of its single crystal. Crystal data of the ester-toluene (1:1, C40H 41NO5, FW 615.77, triclinic, P1, a, 6.194(1) Å, b, 10.686(2) Å, c, 13.007(2) Å, α, 91.913(4)°, β, 91.046(5)°, γ, 99.929(6)°, V, 847.4(3) Å3
- 4 gave the optically pure (S)-4ba (99%). The optically pure (R)-4ba was obtained in a similar manner.

19
- 34247238341
- The enhancement of enantioselectivity by a product-like additive 5 was confirmed even when the asymmetric addition was carried out in ethylbenzene: The reaction in ethylbezene without additive 5 under the same conditions of Entry 1 in Table 1 (the reaction was quenched after stirring for 14h) gave 4aa in 76% yield with the enantioselectivity of 84% ee.
- The enhancement of enantioselectivity by a product-like additive 5 was confirmed even when the asymmetric addition was carried out in ethylbenzene: The reaction in ethylbezene without additive 5 under the same conditions of Entry 1 in Table 1 (the reaction was quenched after stirring for 14h) gave 4aa in 76% yield with the enantioselectivity of 84% ee.

20
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- Examples for asymmetric amplification by a product-like additive: K. Soai, J. Synth. Org. Chem. Jpn. 2004, 62, 673;
- Examples for asymmetric amplification by a product-like additive: K. Soai, J. Synth. Org. Chem. Jpn. 2004, 62, 673;

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