Highly selective catalytic intermolecular reductive coupling of alkynes and aldehydes

Organic Letters

Volumn 2, Issue 26, 2000, Pages 4221-4223

  Huang, Wei Sheng ^a   Chan, Johann ^a   Jamison, Timothy F ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000524458     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006781q     Document Type: Article

References (44)

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30. For example, we tested silanes and boranes in concert with salts of Mg, Cr, Rh, Cu, and Zn.
31. Trace amounts of desired allylic alcohols were observed using triethylsilane as the reducing agent. For examples of uses of triethylborane in Ni(II)-catalyzed reactions see: (a) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033.
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34. Identity established by comparison with known compounds and/or by appropriate NOE NMR experiments. See Supporting Information. Similar regioselectivity trends were observed with terminal alkynes.
35. As the Cahn-Ingold-Prelog priority of Si is higher than that of C, the allylic alcohol products in entries 3, 4, 6, and 9 (Table 2) are assigned the (Z) configuration. As in all other cases, they are nevertheless the products of cis addition to the alkyne.
36. 3P nor BINAP was an effective additive in these reactions.
37. Equivalent results are obtained with the less expensive "tributylphosphine" (contains isomers) as with the more expensive "tri-n-butylphosphine" (isomerically pure). The former was used in all subsequent experiments.
38. 2, and addition to 2d affords 10a as a 64:36 ratio of diastereomers. See Supporting Information and ref 6a.
39. See ref 10 for examples of Ni-catalyzed reductive alkynal cyclizations in natural product synthesis.
40. Access to enantiomerically enriched allylic alcohols is possible in two catalytic reactions by combining this method with an efficient kinetic resolution. (a) Sharpless asymmetric epoxidation (review): Johnson, R. A.; Sharpless, K. B. In Comprehensive Organic Synthesis; Trost. B. M., Ed.; Pergamon: New York, 1991; Vol. 7, Chapter 3.2.
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44. 3B in Ni(II)-catalyzed reactions.