Acylation of Chiral Alcohols: A Simple Procedure for Chiral GC Analysis

Table 5

Separation factor values (α) of the stereoisomers of some cyclic alcohols and their corresponding acetyl derivatives.

Entry		T (°C)	I	Alcohol		α	AC		α
				RT			RT
1		70	trans	5.51	5.51	1.00	4.57	5.17	1.13	a
			cis	5.51	5.51		4.80	6.08	1.27
2		70	trans	5.53	5.53	1.08	4.29	4.29	1.01	a
			cis	5.99	5.99		4.34	4.34
3		70	trans	14.56	14.56	1.03	9.23	10.59	1.15	a
			cis	15.00	15.00		11.83	11.83	—
4		110	trans	4.48	4.48	1.02	3.25	3.78	1.16	b
			cis	4.57	4.57		4.11	4.18	1.02
5		90	(+/−)	3.96	4.52	1.14	3.27	3.48	1.06	a
6		80	trans	15.71	15.71	1.02	4.76	4.76	1.04^d	c
			cis	15.96	15.96		4.93	4.93
7		110	(−)	5.73	—	1.07	4.82	—	1.61	a
			(+)	6.12	—		7.76	—
8		110		2.82	2.82	1.00	1.85	1.94	1.04	a
9		110		4.37	4.53	1.04^e	3.18	3.70	1.16	b

T: GC analysis temperature, (°C); I: isomer; RT: retention time; AC: acetyl derivatives; the elution order of the acetylated enantiomers was assumed from the literature [34, 35]; a: ¹H and ¹³C NMR spectral data in the appendix; b: ¹H and ¹³C NMR spectral data were in agreement with those published in [38]; c: ¹H and ¹³C NMR spectral data were in agreement with those published in [42]; d: 1 : 10 ratio alcohol : acid; e: reversal of the elution order.