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2

Your benzyl acetal groups should be stable to all varieties of hydride reducing agents. For the enoate reduction I suggest Dibal-H or LiBH4/Et2O. I don't have references for this as I no longer have Scifinder access, and Google is not finding me any references that are not behind paywalls.


7

My answer is intended to support Waylander's suggestion elsewhere. I thought it'd be better to give OP some insight of this reduction mentioned (Ref.1). To my knowledge, after doing thorough literature search, the aromatic nitro group reduction by $\ce{SnCl2.2H2O}$ is the best method so far in the presence of other sensitive groups such as nitrile group on ...


5

$\ce{SnCl2.2H2O}$ in refluxing $\ce{EtOAc}$ as reported by Bellamy & Ou here will do this very cleanly. Work up into ice then add concentrated $\ce{NaOH}$ until you get phase separation. I have done this transformation.


5

Ludwig Gattermann's The Practical Methods of Organic Chemistry (translated into English, 1896) has two references to reduction of aromatics with zinc dust: The first one refers to Liebigs Annalen, issue 140, page 295 (1866): Ueber die Reduction aromatischer Verbindungen mittelst Zinkstaub, Adolf Baeyer This roughly translates to "On the reduction of ...


4

Chiral amino alcohols such as L-valinol are generally prepared by the reduction of corresponding α-amino acids and suitable reducing reagent. Most commonly used reducing agent is $\ce{LiAlH4}$ since most common reducing reagent, $\ce{NaBH4}$ does not reduce carboxylic acid to corresponding alcohols. However, use of $\ce{LiAlH4}$ has notable disadvantages ...


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