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. Author manuscript; available in PMC: 2008 Aug 26.
Published in final edited form as: Org Lett. 2005 Jul 7;7(14):2937–2940. doi: 10.1021/ol050881k

Table 2.

Extension of the Anti-Selective Reductive Coupling to a Variety of Aryl Alkynes and α-Oxyaldehydesagraphic file with name nihms-63774-t0007.jpg

entry Ar R1 R2 R3 d.r.b yield (%) (d.r.)c
1 Ph Me Cy MOM 88:12 87(90:10)
2 1-Naphthyl Me Cy MOM 83:17 93(83:17)
3 Ph Et Cy MOM >95:5 54(>95:5)
4 Ph graphic file with name nihms-63774-t0008.jpg Cy MOM >95:5 62(>95:5)
5 Ph CH2NHBoc Cy MOM 90:10 60(95:5)
6 Ph Et Cy PMB >95:5 74(>95:5)
7 Ph Et Ph MOM 68:32 39(>95:5)d
8 Ph Et n-hexyl MOM 75:25 86(80:20)
a

All reactions were conducted with 100 mol% of alkyne and 150 mol% of aldehyde. All reactions proceeded with >95:5 regioselectivity.

b

Ratio of anti:syn determined by 1H NMR analysis ofcrude reaction mixtures.

c

Yield and diastereoselectivity of the isolated reaction product.

d

The syn product was also isolated in 18% yield (>95:5 d.r.).