The addition of the carbenoid species (chlorodiphenylmethyl)lithium to chiral N‐(4‐bromobutylidene)‐2‐methylpropane‐2‐sulfinamide affords in high yield (up to 81%) and excellent diastereoselectivity (>99:1) the yet undisclosed tert‐butylsulfinyl‐2‐(chlorodiphenylmethyl)pyrrolidine. Preliminary investigations into SN1 solvolysis reactions of this chloride with different alcohols revealed its potential for further functionalizations leading to differently substituted chiral pyrrolidines, yet showing a relative lability of the tert‐butylsulfinyl chiral auxiliary under the employed reaction conditions. Most notably, reactions with sterically hindered alcohols yielded unprecedented derivatives, not easily obtainable using the currently reported procedures for the stereoselective synthesis of diphenylprolinol derivatives.

中文翻译：

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叔丁基亚磺酰基-2-(氯二苯甲基)吡咯烷的非对映选择性合成及功能化

将类胡萝卜素 (氯二苯基甲基) 锂添加到手性 N-(4-溴丁亚基)-2-甲基丙烷-2-亚磺酰胺中，以高产率（高达 81%）和优异的非对映选择性（> 99:1）提供尚未公开的叔-丁基亚磺酰基-2-(氯二苯基甲基)吡咯烷。对这种氯化物与不同醇的 SN1 溶剂解反应的初步研究揭示了其进一步官能化的潜力，导致不同取代的手性吡咯烷，但显示出叔丁基亚磺酰基手性助剂在所采用的反应条件下相对不稳定。最值得注意的是，与位阻醇的反应产生了前所未有的衍生物，使用目前报道的二苯基脯氨醇衍生物立体选择性合成程序不容易获得。