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Please login to access the full content or check if you have access via1.13.5.3 Hydroboration/Amination of Alkenes
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Reznichenko, A. L.; Hultzsch, K. C., Science of Synthesis: Stereoselective Synthesis, (2011) 1, 721.
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.[117–121] 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.[122–124]
M eeeeeeeee eee-eee eeeeeeee ee eeeeeeeeeeeeeeee eeeeeeeeeeeee/eeeeeeeee ee eeeeeee eeeeeeee eeeeee eeeeeeeee eeeeeeeeeeeeeeee eeeeeee-eeeeeeeee eeeeeeeeeeeee eeee eeeeeeeeeeeeee eeeeeeeee eeeeeee eeeeeeee 88.[888,888] M eeeeeeeeee eeeeee eeeeeeeeee eeee ee eeeeeeeeee eeeeeee eeeee e eeee eeeeeeee eeeeeeeeeeeeee, eeeee ee eeee eeeeeeeee ee e eeeeeeee eeee e eeeeeeeeee ee eeeeee eeeeee eeeeeee ee eeeeeeeee eeeeee 88 (Meeeee 88).[888,888] Meee eeeeee eee ee eeee ee ee eeeeeeeeeee ee eee Meeeeeeeeee eeeeeeeeeeeeee ee eeeeeeeeeee (eee Meeeeee 8.88.8.8).
Meeeee 88 Meeeeeeeee Meeeeeeeeeeee/Meeeeeeee ee Meeeeeeeeee[888]
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 8 eee% ee eeeeeee eeeeeeee 88 eee eeeeeeee.
Meeeeeeeeeee Meeeeeeee
(M)-M-(8-Meeeeeeeeeeee)-8-(8-eeeeeeeeeeeee)eeeeeeeeee (88, M8 = MMe; M8 = MMM); Meeeeee Meeeeeeee:[888]
Me e eeee ee [Me(eeee)(eee)] (8.8 ee, 8.88 eeee) eee (M)-MMMMMM MMMMMM = 8-[8-(eeeeeeeeeeeeeeeee)-8-eeeeeeee]eeeeeeeeeeee; 8.8 ee, 8.88 eeee ee eeeee MMM (8 eM) eeeee eeeee eee eeeee MMMMMe (8 µM, 8.88 eeee) eeee eeeeeeee. Mee eeeeee eee eeeeeee ee 8.8 eM eeeee eeeeeee eeeeeeee eee eeeeeee (8 × 88 eM) eee eeeee ee eeeeeeeeeee eee eeeeeeee. Mee eeeeeee eee eeeeeee eeee e eeeeeee eee eee eeeeeeee eee eeeeee eeeee eeeeee, eee eeee eeeee eeeee. Meeeeee (8 eM) eee eeeee eeeeeeee ee 8-eeeeeeeeeeeeee (888 ee, 8.8 eeee), eee eeee eeeeeeeeeeeeee (888 µM, 888 ee, 8.8 eeee) eee eeeee eeeeee eeee e eeeeeee. Mee eeeeeee eee eeeeeee eee 8 e eee e 8.8 M eeee ee Me8Me ee eeeeeee (8 eM, 8.8 eeee) eee eeeee eeeeee eeee e eeeeeee. Mee eeeeeee eee eeeeeee eee e eeeeeee 8 e eee e eeeee eeeeeeeeeee eeeeee. Mee eeeeeeeeeeeeeee eee eeeeeeeee ee eee eeeeeeee ee 8 M ee MeMMe (8.8 eeee) ee 8-eeeeeeeeeeeeeeeeee (888 ee, 8.8 eeee) ee Me8M (88 eM) ee 8 °M. Mee eeeeeeeeeee eeee, eeeeeeeee ee 8 °M, eee eeeee ee eee eeeeeeeeee eeee. Mee eeeeeeeeeeee eeeeee eeeeeee eee eeeeeeeee eeee eeeeeee Me8M (88 eM), eeeee eee eeee eeeee ee eee eeeeeeeeee eeee. Mee eeeeeee eee eeeeeee ee 8 °M eee 8 eee, eeeeeee ee eeee ee ee, eee eeee eeeeeee eee e eeeeeee 88 eee. 8 M Me MMe (88 eM) eee eeeee eee eee eeeeeee eee eeeeeee eee 88 eee eee eeee eeeeee eeee Me8M (8 × 88 eM). Me MeMM (8.8 M, 88 eM) eee eeeee ee eee eeeeeee eeeee, eeeee eee eeee eeeeeeeee eeee Me8M (8 × 88 eM), eee eee eeeeeee eeeeeeee eeee eeeee (MeMM8) eee eeeeeeee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eeeeeeeeeeee ee eee eeeee eeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, Me8M/eeeeeee 8:8) eeeeeeee e eeeee, eeeeeeeee eee; eeeee: 8.88 e (88%); 88% ee.
References
[117] | Meeee, M. M.; Meeeeeee, M. M.; Meeeee, M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[118] | Meeeee, M. M.; Meeee, M.; Meeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[119] | Meeeee, M.; Meeeeeeeee, M.; Meeee, M.; Meeee, M., Meeeeeeee, (8888), 888. |
[120] | Meeeeee, M. M.; Meeeeeeee, M. M.; Meeee, M. M., Meeeeeeeeeeeeee, (8888) 8, 8888. |
[121] | Meeee, M. M.; Meeeeee, M. M.; Meee, M. M.; Meeee, M. M.; Meeeeeeee, M. M.; Meeeee, M.; Meee, M.; Meee, M., Meeeeeeeeee, (8888) 88, 8888. |
[122] | Meeee, M. M.; Mee, M. M.; Meee, M. M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[123] | Meeeeeeeeeee, M. M.; Meeeeeee, M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[124] | Meeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[125] | Meeee, M. M.; Meeee, M. M., Me Meeeee Meeeeeeee Meeeeee, Meeeeeeee, M. M.; Meeeeee, M. M., Mee.; Meeee-MMM: Meeeeeee, Meeeeee, (8888); e 88. |
[126] | Meeeeee, M.-M.; MʼMeeeeeee, M. M.; Meeee, M. M., Mee. Meeee. Meeee., (8888) 888, 888. |
[127] | Meeeeeeee, M.; Meeeee, M. M.; Meeeee, M. M.; Meeee, M. M., Meee. Meeeee. (Meeeeeeee), (8888), 888. |
[128] | Meeeeeeee, M.; Meeee, M.; Meeeee, M. M.; Meeee, M. M., Meee.–Mee. M., (8888) 8, 8888. |