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. 2004 Apr 5;101(15):5374–5378. doi: 10.1073/pnas.0307785101

Table 2. Scope of O-nitroso aldol reaction.

Entry 4 Yield, %* 5/7 ee of 5, % (Conf.)§
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4a 94 >99/- >99 (R)
2 4b 87 >99/- >99
3 4c 97 >99/- 99
4 4d 95 >99/- >99
5 4e 75 72/28 >99
6** 4f 67 >99/- 98 (R)
7†† 4g 65 >99/- 98
8** 4h 69 >99/- 98

Reactions were conducted with 5 mol % of 3f, 1.0 eq of nitrosobenzene, and 3 eq of 4 in DMSO at rt.

*

Isolated yield.

Determined by yield of each isolated isomer.

Determined by HPLC (Supporting Text).

§

Determined after conversion to the corresponding diol (Supporting Text).

Reaction was conducted with 20 mol % of 3f in DMSO at rt.

Determined by isolated yield of corresponding primary alcohol obtained after reduction of product.

**

Reactions were conducted with 10 mol % of 3f in MeCN at rt.

††

Reaction was conducted with 20 mol % of 3f in MeCN at rt.