Selective hydroboration of terminal alkenes in the presence of aldehydes and ketones

Divergent and Efficient Syntheses of the Lycopodium Alkaloids (−)‐Lycojaponicumin C, (−)‐8‐Deoxyserratinine, (+)‐Fawcettimine, and (+)‐Fawcettidine

“…However, hydroboration of the olefin 14 did not afford the desired primary alcohol, which might be attributed to the fact that the C13 carbonyl group was unprotected. Thus protection of C13 carbonyl with glycol and then hydroboration of the double bond under conditions reported by Kabalka and co‐workers15 furnished the primary alcohol 15 in 65 % yield over two steps. Mitsunobu reaction16 of the alcohol with diphenylphosphoryl azide (DPPA) produced azidoketone 16 , the structure of which was confirmed by X‐ray crystallographic analysis 17.…”

The 2-(Triphenylsilyl)ethoxycarbonyl-(“Tpseoc”-) Group: A New Silicon-Based, Fluoride Cleavable Oxycarbonyl Protecting Group Highly Orthogonal to the Boc-, Fmoc- and Cbz-Groups

“…2-(Triphenylsilyl)ethanol ( 2 ) [ 8 ],[ 28 ]. A 250 mL round-bottom flask equipped with gas inlet and a stirring bar was charged with triphenylvinylsilane ( 1 , 1.02 g, 3.56 mmol) dissolved in dry THF (20 mL) under an atmosphere of nitrogen.…”

Sodium perborate and sodium percarbonate: further applications in organic synthesis

“…51 For example, 5- View Online methylhex-5-en-2-one is converted into 6-hydroxy-5-methylhexan-2-one, and undec-10-enal to 11-hydroxyundecanal, as shown in Scheme 14, using dicyclohexylborane formed in situ from BH 3 -THF and cyclohexene. Terminal alkynes are similarly transformed into aldehydes.…”