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. 2019 Mar 16;14:88–99. doi: 10.1016/j.isci.2019.03.010

Table 2.

Substrate Scope of Aldehydes in the Reaction with 1a

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R = H,
R = F,
R = Cl,
R = Br,
R = I,
R = Me,
R = tBu,
R = CH3S,
R = CH3O,
R = CF3O,		 3a, 85%, 99% ee;b
3b, 81%, 99% ee;
3c, 74%, 99% ee;
3d, 77%, 98% ee;
3e, 92%, 99% ee;
3f, 80%, 98% ee;
3g, 90%, >99% ee;
3h, 85%, >99% ee;
3i, 81%, 97% ee;
3j, 83%, 99% ee;		 R = F, 3k, 90%, 98% ee;
R = CF3, 3l, 91%, 95% ee;
R = OCH3, 3m, 91%, 98% ee;		 R = Cl, 3n, 81%, 98% ee;
R = Br, 3o, 88%, 97% ee;
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3p, 94%, 99% ee; X = O, 3q, 85%, >99% ee;
X = S, 3r, 91%, >99% ee;
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3S, 76%, 98% ee; 3t, 55%, >99% ee; 3u, 85%, >99% ee;
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X = O, 3v, 81%, 97% ee;
X = S, 3w, 90%, >99% ee;		 3x, 58%, >99% ee; R = H, 3y, 76%, 97% ee;
R = Me, 3z, 78%, 98% ee;
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3aa, 85%, 98% ee; 3ab, 68%, 93% ee; 3ac, 58%, 97% ee;
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3ad, 68%, 95% ee; 3ae, 71%, 93% ee; 3af, 71%, 97% ee;
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3ag, 47%, 98% ee; 3ah, 85%, 98% ee; 3ai, 68%, 99% ee;
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3aj, 52%, 15/1 dr; 3aj′, 60%, >20/1 dr;c 3ak, 58%, >20/1 dr;
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3ak′, 79%, >20/1 dr;c 3al, 88%, >20/1 dr; 3al′, 61%, >20/1 drc

HPLC, high-performance liquid chromatography; NMR, nuclear magnetic resonance

a

2, 0.3 mmol; 1, 0.9 mmol. Isolated yield was reported. Regio- and diastereoselectivity were determined by 1H NMR analysis of reaction crude mixture. Enantioselectivity was determined by chiral-stationary-phase HPLC analysis.

b

Gram-scale synthesis.

c

(S)-DTBM-SEGPHOS was used.