This account chronicles the iterative development of an enantioselective conjugate addition of organoboron nucleophiles to α,β-unsaturated enones and enals catalyzed by BINOL derivatives. Beginning with a specific application of this transformation to the total synthesis of the flinderole alkaloids, the transformation progressed to encompass a much larger scope of heterocycle-substituted electrophiles. The next phase saw progress toward the use of a broader scope of functional nucleophiles, with application in a strategy to synthesize discoipyrrole D. At each stage of this chronologically organized discussion, key problems, hypotheses, and solutions are presented to show the sources of discovery and solutions to problems as the catalyst and other reaction components were made more reactive. The interplay of target-directed reaction development, efforts to increase the scope of compatible functional groups, mechanistic studies, and empirical exploration is described to illustrate sources of chemical discovery. 1 Introduction 2 Synthesis of the Flinderole Natural Products 3 Indole-Bearing Stereocenters 4 Heteroaryl-Bearing Stereocenters 5 Bis-Heteroaryl Stereocenters 6 Synthetic Strategy for Discoipyrrole D 7 Bis-Aryl Stereocenters 8 Remaining Challenges 9 Conclusion

中文翻译：

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追求对映选择性合成含杂环的立体中心：立体控制的 BINOL 催化有机硼亲核试剂的共轭加成的发展

该帐户记录了由 BINOL 衍生物催化的有机硼亲核试剂与 α,β-不饱和烯酮和烯醛的对映选择性共轭加成的迭代发展。从这种转化在氟林德罗生物碱的全合成中的具体应用开始，转化发展到涵盖更大范围的杂环取代亲电试剂。下一阶段在使用更广泛的功能性亲核试剂方面取得了进展，并将其应用于合成discoipyrrole D的策略。在这个按时间顺序组织的讨论的每个阶段，都提出了关键问题、假设和解决方案，以显示发现的来源由于催化剂和其他反应成分的反应性更强，因此可以解决问题。靶向反应发展的相互作用，描述了增加兼容官能团范围、机理研究和经验探索的努力，以说明化学发现的来源。1 引言 2 Flinderole 天然产物的合成 3 含吲哚的立体中心 4 含杂芳基的立体中心 5 双杂芳基立体中心 6 盘吡咯 D 的合成策略 7 双芳基立体中心 8 剩余的挑战 9 结论