Table 2.

Substrate scope with new sulfenylating agents.

Entry	Alkene 3		Sulfenylating agent 7		Product 4		Temp [°C]	Time [h]	Yield [%]e	e.r.i
1		3a		7a		4aab	−20	36	78	95.6:4.4k
2		3a		7f		4afa	−20	36	84	97.6:2.4k
3		3a		7h		4aha	−20	36	87f	98.4:1.6j,k
4		3a		7b		4aba	0	48	87 g	99.3:0.7j,k
5		3g		7a		4gab	0	36	83	88.9:11.1k
6		3g		7b		4gba	0	36	94	98.6:1.4l
7		3b		7a		4bab, c	−20	48	77	97.4:2.6l
8		3b		7b		4bba, c	0	36	85	99.2:0.8l
9		3e		7a		4eab, c	23	24	75 h	87.8:12.2l
10		3e		7b		4eba, c	23	24	84h	98.6:1.4l
11		3h		7a		3haa, d	0	48	85	83.7:16.3k
12		3e		7b		3hba, d	23	24	72	94.3:5.7k

^aGeneral reaction conditions: 3 (1.0 mmol), 7 (1.0 mmol), MsOH (1.0 mmol), (R)-1b (10 mol%), CH₂Cl₂ (0.2 M).

^bReaction of literature described compounds²¹ conducted on 0.2 mmol scale.

^cMeOH used as external nucleophile.

^d0.5 equiv MsOH used.

^eYield of isolated products.

^fCombined yield of a 97:3 mixture of tetrahydropyran/-furan.

^gCombined yield of a 93:7 mixture of tetrahydropyran/-furan.

^hCombined yield of a 4:1 mixture of 4e and its constitutional isomer (Supporting Information).

ⁱAbsolute configuration assigned by comparison and in analogy to literature described compounds.

^je.r. of the major isomer.

^kDetermined by CSP-SFC analysis.

^lDetermined by HPLC analysis.