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1.13.5.3 Hydroboration/Amination of Alkenes

DOI: 10.1055/sos-SD-201-00361

Reznichenko, A. L.; Hultzsch, K. C.Science of Synthesis: Stereoselective Synthesis, (20111721.

The reaction of alkylboranes with electrophilic nitrogen-containing compounds such as chloramines, hydroxylamine-O-sulfonic acids, azides, and hydrazoic acid (HN3), is a well-documented protocol to obtain primary and secondary amines from alkylboron compounds.[‌117‌‌121‌] Enantiopure alkylboranes derived from isopinocampheylboranes have been shown to give chiral amines with complete retention of configuration. However, this approach requires multiple synthetic manipulations at the organoboron group.[‌122‌‌124‌]

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Meeeeeeeeee 88

M8 M8 M8 Meeee (%) ee (%) Mee
M Me M 88 88 [‌888‌]
MMe Me M 88 88 [‌888‌]
M Me Me 88e 88 [‌888‌]
MMe Me MMM 88 88 [‌888‌]

e 8eee% ee eeeeeee eeeeeeee 88 eee eeeeeeee.

Meeeeeeeeeee Meeeeeeee

(M)-M-(8-Meeeeeeeeeeee)-8-(8-eeeeeeeeeeeee)eeeeeeeeee (88, M8=MMe; M8=MMM); Meeeeee Meeeeeeee:[‌888‌]

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References


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