The first example of enantioselective allyl transfer from a linear homoallylic alcohol to an aldehyde

Organic Letters

Volumn 4, Issue 17, 2002, Pages 2985-2987

  Loh, Teck Peng ^a   Lee, Chi Lik Ken ^a   Tan, Kui Thong ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; ALLYL COMPOUND; AMPHIDINOLIDE K; FUSED HETEROCYCLIC RINGS; MACROLIDE;

ARTICLE; CHEMISTRY; STEREOISOMERISM;

ALCOHOLS; ALDEHYDES; ALLYL COMPOUNDS; BICYCLO COMPOUNDS, HETEROCYCLIC; MACROLIDES; STEREOISOMERISM;

EID: 0013282193     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0263999     Document Type: Article

References (27)

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9. For examples of preparation of α-adduct linear homoallylic alcohol, see: (a) Loh, T. P.; Tan, K. T.; Yang, J. Y.; Xiang, C. L. Tetrahedron Lett. 2001, 42, 8701.
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18. We found that this allyl transfer reaction was largely dependent on the steric effect of the substituent on allylic alcohol and aldehyde. In many cases, the improved yields of the desired α-adduct linear homoallylic alcohol arose because the amount of the Prins product decreased.
19. 3 gave no desired α-adduct homoallylic alcohol 4.
20. 2 gave 15, 30, and 69% α-adduct, respectively, together with 37, 10, 10% of prins product, respectively.
21. For some examples of allyl transfer from its kinetic γ-adduct to its thermodynamically stable α-adduct, see: (a) Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609.
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24. (d) Nokami, J.; Ohga, M.; Nakamoto, H.; Matsubara, T.; Hussain, I.; Kataoka, K. J. Am. Chem. Soc. 2001, 123, 9168.
25. 1 (ee > 97%) was prepared using a procedure described by Nokami et al.; see ref 10d.
26. (a) William, D. R.; Meyer, K. G. J. Am. Chem. Soc. 2001, 123, 765.
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