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. Author manuscript; available in PMC: 2008 Dec 8.
Published in final edited form as: Org Lett. 2006 Aug 31;8(18):4089–4091. doi: 10.1021/ol061596j

Table 1.

Allenylboration of RLRSCO with 1

graphic file with name nihms63592f3.jpg
RL RS 1 series 6(%)a % eeb (abs config)
Ph Me S a 74 91 (S)
Ph Me R a 85 93 (R)
Ph Et R b 65 76 (R)
Et Me R c 71 74 (S)
Bu Me S d 80 81 (R)
i-Pr Me R e 71 84 (R)
t-Bu Me S f 66 83 (S)
TMS Me S g 62 90 (R)
CH2=CH Me S h 64 61 (S)
a

The a series was performed with both (−)-1R and (+)-1S. The aS, b, f and h series were conducted employing an oxidative work-up. For the remaining examples, the intermediate 5 was isolated and converted to 6 and either 4 or 8 was recovered (69–81%) via the NMPE work-up procedure.

b

Product ee determined by conversion to the Alexakis esters6 and analysis by 31P NMR.