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

Table 3.

Substrate Scope of Aldehydes in the Reaction with 4a

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R = H,
R = F,
R = Cl,
R = Br,
R = I,
R = Me,
R = tBu,
R = CH3S,
R = CO2Me,		 5a, 95%, 97% ee;b
5b, 88%, 97% ee;
5c, 93%, 97% ee;
5d, 85%, 92% ee;
5e, 82%, 91% ee;
5f, 96%, 97% ee;
5g, 91%, 95% ee;
5h, 90%, 97% ee;
5am, 76%, 98% ee;		 R = F,
R = Br,
R = Me,
R = CF3,		 5K, 95%, 98% ee;
5an, 85%, 92% ee;
5ao, 98%, 99% ee;
5l, 81%, 97% ee;		 R = F,
R = Cl,
R = Br,		 5ap, 80%, 97% ee;
5n, 81%, 98% ee;
5o, 76%, 98% ee;
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5aq, 88%, 97% ee; 5p, 97%, 95% ee;
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X = O, 5q, 81%, 98% ee;
X = S, 5r, 84%, 98% ee;		 5ar, 76%, >99% ee; 5u, 85%, 95% ee;
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5as, 78%, 97% ee; 5x, 46%, 93% ee; R = H, 5y, 84%, 94% ee;
R = Me, 5z, 51%, 95% ee;
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5aa, 80%, 92% ee; R = Me, 5ad, 50%, 93% ee;
R = nPr, 5ae, 70%, 97% ee;		 5at, 88%, 96% ee;
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5au, 80%, 94% ee; 5ah, 70%, 95% ee; 5ak, 56%, >20/1 dr;
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5ak′, 60%, >20/1 dr;c 5al, 68%, >20/1 dr; 5al′, 53%, 10/1 drc

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

a

2, 0.3 mmol; 4, 0.6 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.