Table 6.

Expanded Reaction Scope for Asymmetric Catalytic Diazoester Aldol.

Entrya	RCHO	Product	Time (h)	Yield (%)b	ee (%)c
1	Ph 3a	4a	18	92	95
2d	Ph 3a	4a	24	95	−95
3	m-CH3OC6H4 3b	4b	18	83	90
4	p-CH3OC6H4 3c	4c	18	70	87
5	o-CIC6H4 3d	4d	18	91	89
6	m-FC6H4 3e	4e	24	78	91
7e	p-FC6H4 3f	4f	24	87	94
8	m-CIC6H4 3g	4g	18	88	98
9f	p-CIC6H4 3h	4h	18	85	96
10f	2-Furyl 3i	4i	18	83	96
11f	i-Pr 3j	4j	24	56	97
12	n-Bu 3k	4k	24	50	97
13g	Cyclohexyl 3l	4l	24	49	91
14h	Et 3m	4m	24	52	96
15	cyclopropane 3n	4n	24	52	>99
16h	cyclopropane 3n	4n	24	77	>99
17	E-BDMSCH=CH 3o	4o	24	86	90
18i	PhCHCH 3p	4p	18	50	94

^aAll reactions were conducted using 0.88 mmol both ethyl dlazoacetate 2 and the respective aldehyde 3a–p at a concentration of 1.0 M in THF unless otherwise noted.

^bIsolated yields.

^cDetermined by chiral HPLC.

^dReaction conducted on 1.76 mmol scale of benzaldehyde 3a using (R,R)-1.

^eEthyl diazoacetate 2 added at ~12.5 uL/hr.

^fReactions conducted at 0.5 M.

^gReaction conducted using 10 mol % (R,R)-1, 20 mol % Bu₂Mg, 10 mol % 17 and 2 equiv. of diazoester 2.

^hReactions conducted using 2 equiv aldehyde with respect to ethyl diazoacetate 2.

ⁱSee discussion.