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Enantioselective syntheses of syn- and anti-?-hydroxyallylsilanes via allene hydroboration-aldehyde allylboration reactions.

ABSTRACT: The kinetic hydroboration of allenylsilane 5 with ((d)Ipc)(2)BH at -40 °C provides allylborane 9Z with ?12:1 selectivity. When the hydroboration is performed at temperatures above -40 °C, 9Z isomerizes to the thermodynamically more stable allylborane 9E with >20:1 selectivity. Subsequent treatment of 9Z or 9E with aldehydes at -78 °C provides syn- or anti-?-hydroxyallylsilanes, 7 or 8, respectively.

SUBMITTER: Chen M 

PROVIDER: S-EPMC3075570 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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Enantioselective syntheses of syn- and anti-β-hydroxyallylsilanes via allene hydroboration-aldehyde allylboration reactions.

Chen Ming M   Roush William R WR  

Organic letters 20110316 8

The kinetic hydroboration of allenylsilane 5 with ((d)Ipc)(2)BH at -40 °C provides allylborane 9Z with ≥12:1 selectivity. When the hydroboration is performed at temperatures above -40 °C, 9Z isomerizes to the thermodynamically more stable allylborane 9E with >20:1 selectivity. Subsequent treatment of 9Z or 9E with aldehydes at -78 °C provides syn- or anti-β-hydroxyallylsilanes, 7 or 8, respectively. ...[more]

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