A separation tool involving the use of a vinyl ester amino acid as acyl donor in a bioresolution has been developed. The acidwashable acyl group acts as a removable tag, facilitating separation of the secondary alcohol from the bioresolution product mixture. The use of these acyl donors from cheap, commercially available amino acids has been demonstrated in conjunction with the hydrolase enzyme Candida antarctica lipase B in the selective acylation of a variety of secondary alcohols.
The reactivity of 1,5-bis(trimethylsilyl)propargylic ethers 3 toward bases and electrophiles was investigated. Bispropargylic ethers 4, substituted allenyne ethers 6-8, and alpha-substituted bispropargylic ethers 9 were prepared in good yields, respectively, by protodesilylation, isomerization, or metalation/alkylation of bispropargylic protected alcohol 3. The ambident behavior of metalated synthon 3 was discussed and rationalized. Removal of the protecting groups of 9 easily afforded useful alpha-substituted bispropargylic alcohol.
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