Table 1.

Nucleophile and electrophile scope in acyl aminal synthesis.^a

entry	substrate	solvent	electrophile	nucleophile	major product	yield (dr)b
1	10	CH2Cl2	iPrC(O)Cl	MeOH	11	75% (2:3:1)
2	10	THF	iPrC(O)Cl	MeOH	12	64% (1:4:1)
3c	10	CH2Cl2Mg(ClO4)2	iPrC(O)Cl	MeOH	11	71% (5:7:1)
4	10	CH2Cl2	MeOCH2C(O)Cl	MeOH	13	69% (1:7:1)
5	10	CH2Cl2	CbzCl	MeOH	14	64% (1:5:1)
6	10	CH2Cl2	Ms2O	MeOH	15	24% (2:4:1)
7	10	CH2Cl2	iPrC(O)Cl	tBuOH	16	71% (2:0:1)
8	10	CH2Cl2	iPrC(O)Cl	PhOH	17	69% (5:6:1)
9	10	CH2Cl2	iPrC(O)Cl	PhSH	18	72% (7:0:1)

^aRepresentative procedure: Cp₂Zr(H)Cl (1.2 equiv) was added to a solution of the substrate in the solvent (0.1 M). The mixture stirred for 10 min at rt, then was cooled to 0 °C. The electrophile (1.2–1.5 equiv) was added and stirred for 10 min. The nucleophile (20 equiv) was added and the reaction was stirred for a few additional minutes.

^bYields refer to the sum of the yields of the diastereomers.

^cNucleophilic addition was conducted at −78 °C.