. Author manuscript; available in PMC: 2008 Aug 26.

Published in final edited form as: Chem Rev. 2007 May 27;107(6):2503–2545. doi: 10.1021/cr0509556

Table 7.

Measured k_rel values for a series of epoxides under solvent-free and highly concentrated reaction conditions.


entry	epoxide substituent	conv. (%)^c	diol ee (%)	k_rel
Aliphatic Epoxides
1^a	CH₃	19	99.5	500
2^a	(CH₂)₃CH₃	19	99.2	310
3^b	(CH₂)₁₁CH₃	18	99.5	490
4^b	(CH₂)₂CH=CH₂	20	99.4	420
5^b	CH₂Ph	20	97.4	96
6^b	c-C₆H₁₁	19	99.6	630
7^b	t-C₄H₉	16	97.0	79
Halogenated Epoxides
8^b	CH₂Cl	20	98.7	190
9^b	CH₂Br	20	96	49
10^a	CH₂F	17	98	120
11^a	CF₃	18	99.6	620
Epoxides Bearing Ether and Carbonyl Functionality
12^b	CH₂OBn	20	97	83
13^b	CH₂OTBS	18	99	250
14^b	CH₂OPh	18	98	120
15^b	CH₂O(1-naphthyl)	20	99	250
16^b	CH₂CH₂OBn	19	97	82
17^b	oxiranyl^d	20	98	130
18^b	CH₂OCOn-C₃H₇	54	99.4	68
19^b	CH₂CO₂Et	20	98	130
20^b	CH₂NHBoc	18	74	7.8
21^b	CO₂CH₃	19	98	120
22^b	COCH₃	18	97	81
23^b	COCH₂CH₃	18	96	60
Aryl, Vinyl, and Alkynyl Epoxides
24^b	C₆H₅	20	98	130
25^b	4-ClC₆H₄	18	97	81
26^b	3-ClC₆H₄	17	98	120
27^b	3-(CH₃O)C₆H₄	19	98	120
28^b	3-(NO₂)C₆H₄	19	99	280
29^b	2-ClC₆H₄	18	98	120
30^b	CH=CH₂	18	98	120
31^b	CCTBS	19	99.4	420

Solvent-free.

Highly concentrated with epoxide : THF = 1 : 1 v/v ratio.

Isolated yield of 1,2-diol.

The substrate was d,l-butadiene diepoxide.