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. Author manuscript; available in PMC: 2017 Nov 2.
Published in final edited form as: Angew Chem Int Ed Engl. 2016 Oct 10;55(45):14077–14080. doi: 10.1002/anie.201608446

Table 1.

Evaluation of Reaction Conditions.

graphic file with name nihms835900t1.jpg
Entry PG silane[b] solvent % yield 3[c]
(syn:anti)[d] 		% yield 4[c]
(E:Z)[d]
1 Bn A THF 99 (10:1) <2
2 Bn A CyH 84 (5:1) <2
3 Bn A toluene 92 (6:1) <2
4 Bn A MTBE 88 (13:1) <2
5 4-CF3-Bn A MTBE 98 (7:1) <2
6 2,4-DMB A MTBE 96 (16:1) <2
7 Ph A THF 66 (3:1) 5 (n.d.)
8 S(O)t-Bu A THF <2 8 (n.d.)
9 Boc A THF 4 (n.d.) 25 (4:1)
10 P(O)Ph2 A THF <2 65 (>20:1)
11 P(O)Ph2 B THF[e] <2 85 (>20:1)
[a]

Conditions: 0.1 mmol imine (1.0 equiv), allene (2.0 equiv), copper(II) acetate (0.05 equiv), DCyPE (0.06 equiv), silane (5.0 equiv), tert-butanol (2.0 equiv) in solvent (0.2 mL), see Supporting Information for further details.

[b]

A = (MeO)2MeSiH; B = PhSiH3.

[c]

Yield determined by 1H NMR using 1,1,2,2-tetrachloroethane as an internal standard.

[d]

Diastereomer ratio measured by 1H NMR of the crude reaction mixture.

[e]

Reaction performed using 0.4 mL of solvent.