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. Author manuscript; available in PMC: 2007 May 14.
Published in final edited form as: J Am Chem Soc. 2006 Mar 1;128(8):2751–2756. doi: 10.1021/ja056018x

Table 1.

Optimization Summary for Asymmetric Alkene Acylationa

graphic file with name nihms16460f12.jpg

entry Ar SiR3 NR′2 phosphite time (h) F− source yield (%) %ee
1 Ph SiMe2Ph graphic file with name nihms16460t1.jpg 1-Ph 1.0 TBAF 67 50
2 Ph SiMe2Ph graphic file with name nihms16460t2.jpg 6b 1.0 TBAF 57 −60
3 Ph SiMe2Ph NMe2 6b 2.5 TBAF 40 −71
4 Ph SiEt3 NMe2 6b 2.0 TBAF 44 −88
5 p-MeOPh SiEt3 NMe2 6b 0.75 TBAF 85 −90
6 p-MeOPh SiCyMe2 NMe2 6b 0.25 TBAF 78 −87
7 p-MeOPh SiCyMe2 NMe2 1-Ph 1.0 TBAF 54 81
8 p-MeOPh SiCyMe2 NMe2 6b 0.25 HF·pyr 73 −89
9 p-MeOPh SiCyMe2 NMe2 6a 1.0 HF·pyr 82 88
a

ArC(O)SiR3 (1.0 equiv), PhCH=CHC(O)NR′2 (1.5 equiv), phosphite (0.2 equiv.), and LiN(SiMe3)2 (0.2 equiv) in Et2O from −35 → 25 °C for 0.25–2.0 h after slow addition of alkene and acyl silane.