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. Author manuscript; available in PMC: 2017 Aug 3.

Published in final edited form as: Org Lett. 2017 Jun 2;19(12):3239–3242. doi: 10.1021/acs.orglett.7b01342

Table 3.

Scope of 1,2-syn:2,3-syn Fluorinated Amine Triads


product	yield dr	product	yield dr
	19% 11a (dr 3:1)^b,^c		68% 12a (dr 9:1)^c,^d
	58% 13a (dr 8:1)^b,^c		69% 14a (dr 7:1.5:1)^c,^d
	69% 15a (dr 11:1)^c,^d		56% 16a (dr >19:1)^c,^d
	52% 16b (dr >19:1)^d,^e		89% 16c (dr >19:1)^d,^e,^g
	27% 17a (dr >19:1)^d,^e		28% 17b (dr 4:1)^d,^f
	75% 17c (dr 5:1)^d,^e,^g		51% 18a (dr 3:1)^c,^d
	24% 19a (dr 3:1)^c,^d		41% 20a (dr 6:3:2:1)^c,^d

^a

Listed yields are for the isolated major diastereomer.

^b

Diastereomer ratios of the crude product are in parentheses.

^c

0.1 M MeCN/AcOH, 3 equiv of Me₄N (OAc)₃BH, 0 °C to rt, 12 h.

^d

Isolated dr.

^e

Fluorination in MeCN, 40 0 °C, 14 h.

^f

0.1 M THF, 3 equiv of HCCMgBr, 0 °C, 1 h.

^g

0.1 M MeCN, 2.0 equiv of Bu₄NCN, rt, 2.6 h.